Selectively cleavabe linners based on iminodiacetic acid esters for solid phase peptide synthesis

Claim 2

A solid phase support having the structure: ##STR15## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; PG 2 is a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; f is 2-6; each w is independently 0 or a positive integer; Y is selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; q is 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 3

The solid phase support of claim 1, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 4

The solid phase support of claim 2 wherein A 1 is proline.

Claim 5

A solid phase support having the structure: ##STR16## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; PG 2 is a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; each A 2 is independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; Y is selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 6

A solid phase support having the structure: ##STR16## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; PG 2 is a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; each A 2 is independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; Y is selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 7

The solid phase support of claim 4, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 8

A solid phase support having the structure: ##STR17## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; PG 2 is a protecting group selected from consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; f is 2-6; each w is independently 0 or a positive integer; Y is selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; q is 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 9

A solid phase support having the structure: ##STR17## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; PG 2 is a protecting group selected from consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; f is 2-6; each w is independently 0 or a positive integer; Y is selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; q is 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 10

The solid phase support of claim 6, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 11

The solid phase support of claim 7 wherein A 1 is glycine.

Claim 12

A solid phase support having the structure: ##STR18## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 13

A solid phase support having the structure: ##STR18## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 14

The solid phase support of claim 9, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 15

The solid phase support of claim 10 wherein A 1 is proline.

Claim 16

A solid phase support having the structure: ##STR19## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 17

A solid phase support having the structure: ##STR19## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; A 1 and each A 2 are independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 18

The solid phase support of claim 12, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 19

The solid phase support of claim 13 wherein A 1 is glycine.

Claim 20

The solid phase support of claim 4, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; q is 0; and Y is the 3-hydroxypropylamide of succinic acid.

Claim 21

A solid phase support having the structure: ##STR20## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; each A 2 is independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 22

A solid phase support having the structure: ##STR20## wherein PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; each A 2 is independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, hydroxyacetic acid, serine and the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 23

The solid phase support of claim 16, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 24

A solid phase support having the structure: wherein ##STR21## PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; each A 2 is independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, 2-hydroxy acetic acid, 3-hydroxy, or the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 25

A solid phase support having the structure: wherein ##STR21## PG 1 is a protecting group selected from the group consisting of Boc, Npys, Alloc, Z and modified Z group; each PG 2 is independently a protecting group selected from the group consisting of Fmoc, Boc, Npys, Alloc, Z and modified Z group; each A 2 is independently an α-amino acid; each f is independently 2-6; each w is independently 0 or a positive integer; each Y is independently selected from the group consisting of p-hydroxymethylbenzoic acid, 2-hydroxy acetic acid, 3-hydroxy, or the 3-hydroxypropylamide of succinic acid; each q is independently 0 or 1; and Q is selected from the group consisting of polystyrene resin, poly(dimethylacrylamide)-grafted styrene co-divinylbenzene, polyamide resin, polystyrene resin grafted with polyethylene glycol, polydimethylacrylamide resin, and polysaccharides.

Claim 26

The solid phase support of claim 16, wherein PG 1 is BOC; PG 2 is Fmoc; f is 3; and q is 0.

Claim 27

The solid phase support of claim 1 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 28

The solid phase support of claim 20, wherein said second linker is selected from the group consisting of ONb, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 29

The solid phase support of claim 21, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 30

The solid phase support of claim 1, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR22## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O)R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 3 is a C 1 -C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.

Claim 31

The solid phase support of claim 4 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 32

The solid phase support of claim 24, wherein said second linker is selected from the group consisting of ONb, an Asp-Pro dipeptide, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 33

The solid phase support of claim 25, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 34

The solid phase support of claim 4, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR23## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O)R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 3 is a C 1 -C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.

Claim 35

The solid phase support of claim 6 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 36

The solid phase support of claim 28, wherein said second linker is selected from the group consisting of ONb, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 37

The solid phase support of claim 29, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 38

The solid phase support of claim 6, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR24## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O)R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 3 is a C 1 -C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.

Claim 39

The solid phase support of claim 9 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 40

The solid phase support of claim 32, wherein said second linker is selected from the group consisting of ONb, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 41

The solid phase support of claim 33, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 42

The solid phase support of claim 9, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR25## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O)R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 3 is a C 1 --C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.

Claim 43

The solid phase support of claim 12 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 44

The solid phase support of claim 36, wherein said second linker is selected from the group consisting of ONb, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 45

The solid phase support of claim 37, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 46

The solid phase support of claim 12, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR26## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O) R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 3 is a C 1 -C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.

Claim 47

The solid phase support of claim 16 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 48

The solid phase support of claim 40, wherein said second linker is selected from the group consisting of ONb, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 49

The solid phase support of claim 41, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 50

The solid phase support of claim 16, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR27## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O)R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R z is a C 1 -C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.

Claim 51

The solid phase support of claim 18 which further comprises a second linker that is acid-labile, base-labile, photolabile, or which second linker can be cleaved by an oxidizing agent, a reducing agent, a nucleophile, or an electrophile.

Claim 52

The solid phase support of claim 44, wherein said second linker is selected from the group consisting of ONb, hydroxymethylbenzoic acid, hydroxyacetic acid, and a dipeptide in which the C-terminal amino acid residue is covalently attached via an ester bond to the solid phase support.

Claim 53

The solid phase support of claim 45, wherein said second linker is a dipeptide selected from the group consisting of Glu-Pro and Asp-Pro.

Claim 54

The solid phase support of claim 18, which further comprises a second linker which is a benzhydrylamine handle of the structure: ##STR28## wherein the phenyl group bearing (X 1 ) a , ZZ and optionally (Y) c is referred to as a first phenyl group, and the phenyl group bearing (X 2 ) b and optionally (Y) d is referred to as a second phenyl group; X 1 is selected from the group consisting of --SR 1 , --S(O)R 1 , and --S(O) 2 R 1 , each X 1 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 1 is a C 1 -C 10 hydrocarbon group; ZZ is --OR 3 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the first phenyl group; R 3 is a C 1 -C 10 hydrocarbon group substituted with a carboxyl group for coupling to a solid phase support; X 2 is selected from the group consisting of --SR 2 , --S(O)R 2 , and --S(O) 2 R 2 , each X 2 being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, on the second phenyl group; R 2 is a C 1 -C 10 hydrocarbon group; Y is --OR 4 , being in an ortho or para position, with respect to the carbon atom of the handle bearing NHD, not occupied by (X 1 ) a or ZZ on the first phenyl group and in an ortho or para position, with respect to the carbon atom of the handle bearing KTHD, not occupied by (X 2 ) b on the second phenyl group; R 4 is a C 1 -C 10 hydrocarbon group; a=1-2; b=1-3; c=0-1 d=0-1; and D is selected from the group consisting of --H, a protecting group and an N.sup.α -protected aminoacyl moiety, wherein said handle is covalently bonded to said solid phase support via a linkage formed between the ZZ carboxyl group of said handle, and Q.