US4351762A
Expired / Lapsed
US
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Rapid, quantitative peptide synthesis using mixed anhydrides
Assignee: Bioresearch Inc
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Filing: 1981-03-10
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Granted: 1982-09-28
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Expires: 2001-03-10
Abstract
Abstract In the synthesis of a polypeptide chain wherein an N alpha -urethane-protected amino acid mixed anhydride is coupled with an amino-unprotected second amino acid, the improvement comprising conducting said coupling at room temperature or above. This method provides rapid, essentially quantitative reactions without the necessity for reduced temperatures. The method is particularly useful in the solid-phase synthesis of peptides where shortened coupling cycles and improved yields of substantially pure products are obtained.
Inventors
- 👤 Michael S. Verlander
- 👤 William D. Fuller
- 👤 Murray Goodman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:13
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/0606; C07K1/00; C07K1/06; C07K1/08; C07K5/10; C07K5/1002; C07K5/1005; C07K5/101
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
96 words
In the synthesis of a polypeptide chain on an insoluble solid support containing reactive substituent groups, wherein an N.sup.α -urethane-protected amino acid coupled to the support by condensation with said reactive substituent groups is deprotected to provide a free α-amino group on said coupled amino acid, a second, similar or dissimilar N.sup.α -urethane-protected amino acid in the form of its mixed anhydride is coupled to said α-amino group and the deprotection and coupling processes repeated until the desired polypeptide is obtained, the improvement wherein the mixed anhydride coupling reactions are conducted at room temperature and above.
Claim 2
Dependent Claim
96 words
In the synthesis of a polypeptide chain on an insoluble solid support containing reactive substituent groups, wherein an N.sup.α -urethane-protected amino acid coupled to the support by condensation with said reactive substituent groups is deprotected to provide a free α-amino group on said coupled amino acid, a second, similar or dissimilar N.sup.α -urethane-protected amino acid in the form of its mixed anhydride is coupled to said α-amino group and the deprotection and coupling processes repeated until the desired polypeptide is obtained, the improvement wherein the mixed anhydride coupling reactions are conducted at room temperature and above.
Claim 3
Dependent Claim
18 words
A synthesis according to claim 1 wherein the mixed anhydride is an N.sup.α -t-butyloxycarbonyl amino acid mixed anhydride.
Claim 4
Dependent Claim
18 words
A synthesis according to claim 1 wherein the mixed anhydride is an N.sup.α -benzyloxycarbonyl amino acid mixed anhydride.
Claim 5
Dependent Claim
18 words
A synthesis according to claim 1 wherein the mixed anhydride is an N.sup.α -9-fluorenylmethyloxycarbonyl amino acid mixed anhydride.
Claim 6
Dependent Claim
18 words
A synthesis according to claim 1 wherein the mixed anhydride is an N.sup.α -biphenylisopropyloxycarbonyl amino acid mixed anhydride.
Claim 7
Dependent Claim
14 words
A synthesis according to claim 1 wherein the insoluble support is a crosslinked polystyrene.
Claim 8
Dependent Claim
14 words
A synthesis according to claim 1 wherein the insoluble support is a crosslinked polyacrylamide.
Claim 9
Dependent Claim
16 words
A synthesis according to claim 1 wherein the synthesis is carried out in a flow reactor.
Claim 10
Dependent Claim
16 words
A synthesis according to claim 8 wherein the flow reactor is a pressurized, continuous flow reactor.
Claim 11
Dependent Claim
20 words
A synthesis according to claim 9 wherein the pressurized flow reactor is under a pressure of at least 40 psi.
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) | 1985-09-27 | 1986-03-29 | 1986-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-27 | 1990-03-29 | 1990-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-27 | 1994-03-29 | 1994-09-28 | $7700.00 | Window Closed / Lapsed |