US5753788A
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Photolabile nucleoside protecting groups
Assignee: Affymetrix Inc
•
Filing: 1995-05-19
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Granted: 1998-05-19
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Expires: 2015-05-19
Abstract
Abstract A synthetic strategy for the creation of large scale chemical diversity. Solid-phase chemistry, photolabile protecting groups, and photolithography are used to achieve light-directed spatially-addressable parallel chemical synthesis. Binary masking techniques are utilized in one embodiment. A reactor system, photoremovable protective groups, and improved data collection and handling techniques are also disclosed. A technique for screening linker molecules is also provided.
Inventors
- 👤 Stephen P. A. Fodor
- 👤 Christopher P. Holmes
- 👤 Dennis W. Solas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:46
CPC Classifications
G; G01; G01N; G01N21/00; G01N21/62; G01N21/63; G01N21/64; G01N21/645; G01N21/6452; B; B01; B01J; B01J19/00; B01J19/0046; B82; B82Y; B82Y10/00; B82Y30/00; C; C07; C07C; C07C229/00; C07C229/02; C07C229/04; C07C229/06; C07C229/10; C07C229/14; C07C229/16; C07D; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/44; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/62; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/073; C07H19/16; C07H19/173; C07H21/00; C07H21/04; C07K; C07K1/00; C07K1/04; C07K1/042; C07K1/045; C07K1/047; C07K1/06; C07K1/061; C07K1/062; C07K17/00; C07K17/02; C07K17/06; C07K17/14; C07K7/00; C07K7/04; C07K7/06; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6809; C12Q1/6813; C12Q1/6816; C12Q1/6834; C12Q1/6837; C12Q1/6869; C12Q1/6874; C40; C40B; C40B80/00; G01N21/17; G01N21/25; G01N21/251; G01N21/253; G01N21/6428; G03; G03F; G03F7/00; G03F7/004; G03F7/0045; G03F7/26; G03F7/265; G03F7/38; G11; G11C; G11C13/00; G11C13/0002; G11C13/0009; G11C13/0014; G11C13/0019; B01J2219/00; B01J2219/00274; B01J2219/00277; B01J2219/00279; B01J2219/00306; B01J2219/00313; B01J2219/00315; B01J2219/00351; B01J2219/00427; B01J2219/00432; B01J2219/00434; B01J2219/00436; B01J2219/00457; B01J2219/00459; B01J2219/00468; B01J2219/00475; B01J2219/00497; B01J2219/005; B01J2219/00527; B01J2219/00529; B01J2219/00531; B01J2219/00583; B01J2219/00585; B01J2219/0059; B01J2219/00596; B01J2219/00603; B01J2219/00605; B01J2219/00608; B01J2219/00612; B01J2219/00614; B01J2219/00617; B01J2219/00623; B01J2219/00626; B01J2219/00632; B01J2219/00637; B01J2219/00646; B01J2219/00648; B01J2219/00659; B01J2219/0068; B01J2219/00686; B01J2219/00689; B01J2219/00695; B01J2219/00709; B01J2219/00711; B01J2219/00718; B01J2219/0072; B01J2219/00722; B01J2219/00725; C07B; C07B2200/00; C07B2200/11; C40B40/00; C40B40/04; C40B40/06; C40B40/10; C40B60/00; C40B60/14; G01N15/00; G01N15/10; G01N15/14; G01N15/1429; G01N15/1433; G01N21/6456; G01N21/6458; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55; Y10; Y10S; Y10S435/00; Y10S435/969; Y10S435/973; Y10S436/00; Y10S436/807; Y10S436/809
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
82 words
A compound comprising the following structure: ##STR25## wherein: n is either 0 or 1; Y is selected from the group consisting of carboxyl group of an amino acid and hydroxyl group of a nucleoside or nucleotide; R 1 and R 2 are selected independently from the group consisting of: lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thio, thioether, amino, nitro, carboxyl, formate, formamido, hydrogen, or phosphido; and R 3 is selected from the group consisting of alkoxy, alkyl, aryl, hydrogen, or alkenyl.
Claim 2
Dependent Claim
82 words
A compound comprising the following structure: ##STR25## wherein: n is either 0 or 1; Y is selected from the group consisting of carboxyl group of an amino acid and hydroxyl group of a nucleoside or nucleotide; R 1 and R 2 are selected independently from the group consisting of: lower alkyl, aryl, benzyl, halogen, hydroxyl, alkoxyl, thio, thioether, amino, nitro, carboxyl, formate, formamido, hydrogen, or phosphido; and R 3 is selected from the group consisting of alkoxy, alkyl, aryl, hydrogen, or alkenyl.
Claim 3
Dependent Claim
35 words
The compound of claim 1, wherein Y is a hydroxyl group of a molecule, said molecule being selected from the group consisting of nucleosides, nucleoside analogs, oligonucleotides, and natural or unnatural amino acids or peptides.
Claim 4
Dependent Claim
52 words
The compound of claim 2, wherein Y is a 5'-hydroxyl group of an oligonucleotide, and wherein said compound is represented by the following structure: ##STR26## wherein R 5 is selected from the group consisting of hydrogen, hydroxyl, substituted hydroxyl, X is a nucleic acid or analog thereof, and B is a base.
Claim 5
Dependent Claim
13 words
The compound of claim 3, wherein R 1 and R 2 are hydrogen.
Claim 6
Dependent Claim
52 words
The compound of claim 2, wherein Y is a 3'-hydroxyl group of an oligonucleotide, and wherein said compound is represented by the following structure: ##STR27## wherein R 5 is selected from the group consisting of hydrogen, hydroxyl, substituted hydroxyl, X is a nucleic acid or analog thereof, and B is a base.
Claim 7
Dependent Claim
13 words
The compound of claim 5, wherein R 1 and R 2 are hydrogen.
Claim 8
Dependent Claim
26 words
The compound of claim 1, wherein R 1 and R 2 are selected independently from the group consisting of: methoxy, lower alkyl, hydrogen, alkoxy, and halogen.
Claim 9
Dependent Claim
19 words
The compound of claim 1, wherein n is 1 and said compound is represented by the following structure: ##STR28##
Claim 10
Dependent Claim
17 words
The compound of claim 2, wherein Y is the hydroxyl group of a nucleoside or nucleoside analog.
Claim 11
Dependent Claim
66 words
The compound of claim 9, wherein Y is the 5'-hydroxyl group of a nucleoside or nucleoside analog, and wherein said compound is represented by the following structure: ##STR29## wherein B is a base, R 4 is selected from the group consisting of hydrogen, hydroxyl, substituted hydroxyl, and activated-phosphorous-containing groups; and R 5 is selected independently from the group consisting of hydrogen, hydroxyl and substituted hydroxyl groups.
Claim 12
Dependent Claim
14 words
The compound of claim 10, wherein R 5 is selected from hydrogen and hydroxyl.
Claim 13
Dependent Claim
20 words
The compound of claim 10, wherein at least one of R 4 and R 5 is a substituted hydroxyl group.
Claim 14
Dependent Claim
12 words
The compound of claim 10, wherein R 4 is an activated-phosphorous-containing group.
Claim 15
Dependent Claim
21 words
The compound of claim 13, wherein said activated-phosphorous-containing group is a phosphotriester group and said compound has the following structure: ##STR30##
Claim 16
Dependent Claim
18 words
The compound of claim 14, wherein R 1 and R 2 are hydrogen and R 3 is methyl.
Claim 17
Dependent Claim
21 words
The compound of claim 13, wherein said activated-phosphorous-containing group is a phosphoramidite group, and said compound has the following structure: ##STR31##
Claim 18
Dependent Claim
18 words
The compound of claim 16, wherein R 1 and R 2 are hydrogen and R 3 is methyl.
Claim 19
Dependent Claim
9 words
The compound of claim 17, wherein B is adenine.
Claim 20
Dependent Claim
9 words
The compound of claim 17, wherein B is thymine.
Claim 21
Dependent Claim
9 words
The compound of claim 17, wherein B is guanine.
Claim 22
Dependent Claim
9 words
The compound of claim 17, wherein B is cytosine.
Claim 23
Dependent Claim
9 words
The compound of claim 17, wherein B is uracil.
Claim 24
Dependent Claim
10 words
The compound of claim 17, wherein R 5 is hydrogen.
Claim 25
Dependent Claim
10 words
The compound of claim 17, wherein R 5 is hydroxyl.
Claim 26
Dependent Claim
11 words
The compound of claim 17, wherein R 5 is substituted hydroxyl.
Claim 27
Dependent Claim
22 words
The compound of claim 14, wherein R 1 -R 3 are hydrogen, and said compound is represented by the following structure: ##STR32##
Claim 28
Dependent Claim
22 words
The compound of claim 16, wherein R 1 -R 3 are hydrogen, and said compound is represented by the following structure: ##STR33##
Claim 29
Dependent Claim
9 words
The compound of claim 27, wherein B is adenine.
Claim 30
Dependent Claim
9 words
The compound of claim 27, wherein B is thymine.
Claim 31
Dependent Claim
9 words
The compound of claim 27, wherein B is guanine.
Claim 32
Dependent Claim
9 words
The compound of claim 27 wherein B is cytosine.
Claim 33
Dependent Claim
9 words
The compound of claim 27, wherein B is uracil.
Claim 34
Dependent Claim
10 words
The compound of claim 27, wherein R 5 is hydrogen.
Claim 35
Dependent Claim
10 words
The compound of claim 27, wherein R 5 is hydroxyl.
Claim 36
Dependent Claim
11 words
The compound of claim 27, wherein R 5 is substituted hydroxyl.
Claim 37
Dependent Claim
18 words
The compound of claim 3, wherein R 1 and R 2 are hydrogen and R 3 is methyl.
Claim 38
Dependent Claim
12 words
The compound of claim 3, wherein R 1 -R 3 are hydrogen.
Claim 39
Dependent Claim
20 words
The compound of claim 2, wherein Y is a carboxyl group of a natural or unnatural amino acid or peptide.
Claim 40
Dependent Claim
20 words
The compound of claim 1, wherein n is 0, and wherein said compound is represented by the following structure: ##STR34##
Claim 41
Dependent Claim
20 words
The compound of claim 39, wherein Y is the carboxyl group of a natural or unnatural amino acid or peptide.
Claim 42
Dependent Claim
20 words
The compound of claim 40, wherein Y is the carboxyl terminus of a natural or unnatural amino acid or peptide.
Claim 43
Dependent Claim
23 words
The compound of claim 40, wherein said natural or unnatural amino acid is selected from the group consisting of the naturally-occurring L-amino acids.
Claim 44
Dependent Claim
45 words
The compound of claim 39, wherein R 1 and R 2 are hydrogen, R 3 is methyl, and wherein said compound is represented by the structure: ##STR35## wherein R 7 is a side chain of a naturally-occurring amino acid and R 8 is an amine.
Claim 45
Dependent Claim
41 words
The compound of claim 39, wherein R 1 -R 3 are hydrogen, and wherein said compound is represented by the following structure: ##STR36## wherein R 7 is a side chain of a naturally-occurring amino acid, and R 8 is an amine.
Claim 46
Dependent Claim
17 words
The compound of claim 41, wherein said natural or unnatural amino acid or peptide is a peptide.
Claim 47
Dependent Claim
11 words
The compound of claim 41, wherein said peptide is a dimer.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-05-18 | 2001-11-17 | 2002-05-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-05-18 | 2005-11-17 | 2006-05-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-05-18 | 2009-11-17 | 2010-05-19 | $7700.00 | Window Closed / Lapsed |