Novel synthesis of optically active γ-carboxyglutamic acid and its derivatives
A novel synthesis of optically active L-γ-carboxyglutamic acid (GLA), found in prothrombin and other vitamin K-dependent factors, is described. This method involves the formation of γ-carbanion of the protected glutamic acid esters by means of a non-nucleophilic base, followed by the treatment with...
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| Published in | Biochemical and biophysical research communications Vol. 94; no. 4; pp. 1128 - 1132 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Elsevier Inc
30.06.1980
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| Subjects | |
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| Abstract | A novel synthesis of optically active L-γ-carboxyglutamic acid (GLA), found in prothrombin and other vitamin K-dependent factors, is described. This method involves the formation of γ-carbanion of the protected glutamic acid esters by means of a non-nucleophilic base, followed by the treatment with benzyl chloroformate or other electrophilic agents, and deprotection by hydrogenation or hydrolysis. This convenient technique is potentially useful for preparation of not only the γ-carboxyglutamic acid itself, but also of the mixed protected ester and amino functions for further peptide syntheses containing this amino acid. |
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| AbstractList | A novel synthesis of optically active L-γ-carboxyglutamic acid (GLA), found in prothrombin and other vitamin K-dependent factors, is described. This method involves the formation of γ-carbanion of the protected glutamic acid esters by means of a non-nucleophilic base, followed by the treatment with benzyl chloroformate or other electrophilic agents, and deprotection by hydrogenation or hydrolysis. This convenient technique is potentially useful for preparation of not only the γ-carboxyglutamic acid itself, but also of the mixed protected ester and amino functions for further peptide syntheses containing this amino acid. |
| Author | Zee-Cheng, Robert K.-Y. Olson, Robert E. |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/7396954$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1016/S0083-6729(08)60521-X 10.1016/S0021-9258(17)33132-0 10.1021/jo00928a032 10.1016/S0040-4039(01)97034-0 10.1016/S0040-4039(01)97075-3 10.1002/hlca.19770600310 10.1016/S0021-9258(19)42259-X 10.1016/0006-291X(75)90401-5 10.1021/jo00884a038 10.1016/0014-5793(74)80723-4 10.1016/S0021-9258(19)41168-X 10.1021/jo00910a030 10.1021/jo00907a039 10.1002/hlca.19760590319 10.1021/ja00509a062 10.1021/jo01362a052 10.1016/0014-5793(77)80092-6 10.1002/hlca.19750580525 10.1016/S0021-9258(17)41030-1 |
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| Title | Novel synthesis of optically active γ-carboxyglutamic acid and its derivatives |
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