US5767288A
Expired / Lapsed
US
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Photolabile linkers and probes
Assignee: California Institute of Technology
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Filing: 1996-01-05
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Granted: 1998-06-16
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Expires: 2016-01-05
Abstract
Abstract The invention relates to dithiane adducts of substituted benzoins and substituted benzoins derived therefrom each of which are useful as protecting groups, photolabile linkers, and fluorescent probes.
Inventors
- 👤 Ronald S. Rock
- 👤 Michael H. B. Stowell
- 👤 Sunney I. Chan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 11:44
CPC Classifications
C; C07; C07H; C07H21/00; C07C; C07C235/00; C07C235/02; C07C235/04; C07C235/18; C07C235/20; C07C45/00; C07C45/56; C07C45/567; C07C49/00; C07C49/76; C07C49/82; C07C49/83; C07C49/84; C07D; C07D339/00; C07D339/08; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/094; C07K; C07K7/00; C07K7/04; C07K7/06; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/58; G01N33/582; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
165 words
A compound having the formula ##STR10## wherein R 1 is hydrogen, carboxy, substituted carbonyl, a phosphorus containing group, a sulfur containing group, a fluorescent label or a biomolecule; R 2 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 3 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 4 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 5 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 6 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; wherein at least one of R 2 or R 6 is hydrogen; and wherein at least one of R 2 , R 3 , R 4 , R 5 or R 6 is hydroxy or substituted alkoxy.
Claim 2
Dependent Claim
165 words
A compound having the formula ##STR10## wherein R 1 is hydrogen, carboxy, substituted carbonyl, a phosphorus containing group, a sulfur containing group, a fluorescent label or a biomolecule; R 2 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 3 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 4 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 5 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 6 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; wherein at least one of R 2 or R 6 is hydrogen; and wherein at least one of R 2 , R 3 , R 4 , R 5 or R 6 is hydroxy or substituted alkoxy.
Claim 3
Dependent Claim
29 words
A compound according to claim 1 wherein said substituted alkoxy is substituted with amino, alkyl amino, carboxy, substituted carbonyl, a phosphorus containing group, a sulfur-containing moiety, or a biomolecule.
Claim 4
Dependent Claim
15 words
A compound according to claim 1 wherein said R 1 group is a fluorescent label.
Claim 5
Dependent Claim
205 words
A compound having the formula: ##STR11## wherein R 1 is hydrogen, carboxy, substituted carbonyl, phosphorus-containing moiety, a sulfur containing group, a fluorescent label or a biomolecule; R 22 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 23 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 24 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 25 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 26 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 27 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 28 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 29 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 30 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 31 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; wherein at least one of R 22 or R 26 is hydrogen; wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is alkoxy or substituted alkoxy; and wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is a biomolecule.
Claim 6
Dependent Claim
205 words
A compound having the formula: ##STR11## wherein R 1 is hydrogen, carboxy, substituted carbonyl, phosphorus-containing moiety, a sulfur containing group, a fluorescent label or a biomolecule; R 22 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 23 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 24 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 25 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 26 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 27 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 28 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 29 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 30 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 31 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; wherein at least one of R 22 or R 26 is hydrogen; wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is alkoxy or substituted alkoxy; and wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is a biomolecule.
Claim 7
Dependent Claim
20 words
A compound according to claim 4 wherein said biomolecule is selected from the group consisting of polypeptides and nucleic acids.
Claim 8
Dependent Claim
158 words
A compound having the formula ##STR12## wherein R 1 is phosphorus-containing moiety, a sulfur containing group, a fluorescent label or a biomolecule; R 2 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 3 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 4 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 5 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 6 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; wherein at least one of R 2 or R 6 is hydrogen; wherein at least one of R 2 , R 3 , R 4 , R 5 or R 6 is hydroxy or substituted alkoxy.
Claim 9
Dependent Claim
158 words
A compound having the formula ##STR12## wherein R 1 is phosphorus-containing moiety, a sulfur containing group, a fluorescent label or a biomolecule; R 2 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 3 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 4 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 5 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 6 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; wherein at least one of R 2 or R 6 is hydrogen; wherein at least one of R 2 , R 3 , R 4 , R 5 or R 6 is hydroxy or substituted alkoxy.
Claim 10
Dependent Claim
12 words
A compound according to claim 6 wherein R 1 is a biomolecule.
Claim 11
Dependent Claim
15 words
A compound according to claim 6 wherein said substituted alkoxy is substituted with a biomolecule.
Claim 12
Dependent Claim
205 words
A compound having the formula ##STR13## wherein R 1 is hydrogen, carboxy, substituted carbonyl, phosphorus-containing moiety, a sulfur containing group, a fluorescent label or a biomolecule; R 22 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 23 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 24 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 25 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 26 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 27 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 28 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 29 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 30 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 31 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; wherein at least one of R 22 or R 26 is hydrogen; wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is alkoxy or substituted alkoxy; and wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is a biomolecule.
Claim 13
Dependent Claim
205 words
A compound having the formula ##STR13## wherein R 1 is hydrogen, carboxy, substituted carbonyl, phosphorus-containing moiety, a sulfur containing group, a fluorescent label or a biomolecule; R 22 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 23 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 24 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 25 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 26 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 27 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 28 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 29 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 30 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 31 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; wherein at least one of R 22 or R 26 is hydrogen; wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is alkoxy or substituted alkoxy; and wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is a biomolecule.
Claim 14
Dependent Claim
12 words
A furan obtained by the photolysis of a compound of claim 9.
Claim 15
Dependent Claim
209 words
A method for forming the compound of claim 1 or claim 4 comprising contacting ##STR14## under conditions that allow the reaction of said components to form a dithiane-benzoin adduct; wherein R 22 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 23 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 24 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 25 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 26 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 27 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 28 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 29 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 30 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; R 31 is hydrogen, alkyl, aryl, alkoxy, substituted alkoxy, or a biomolecule; wherein at least one of R 22 or R 26 is hydrogen; wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is alkoxy or substituted alkoxy; and wherein at least one of R 22 , R 23 , R 24 , R 25 or R 26 is a biomolecule.
Claim 16
Dependent Claim
166 words
A method for forming the compound of claim 1 or claim 4 comprising contacting ##STR15## under conditions that allow the reaction of said components to form a dithiane-benzoin adduct; wherein R 2 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 3 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 4 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 5 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 6 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; R 11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy; wherein at least one of R 2 or R6 is hydrogen; and wherein at least one of R 2 , R 3 , R 4 , R 5 or R 6 is hydroxy or substituted alkoxy.
Claim 17
Dependent Claim
34 words
A method of forming the compound of claim 6 or 9 comprising contacting the corresponding dithiane-benzoin adduct of claims 1 or 4 with a reagent capable of removing said dithiane to form the benzoin.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-06-15 | 2001-12-15 | 2002-06-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-06-15 | 2005-12-15 | 2006-06-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-06-15 | 2009-12-15 | 2010-06-16 | $7700.00 | Window Closed / Lapsed |