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Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl alpha-acetamido, alpha-alkylmalonates
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UNSPECIFIED (2000) Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl alpha-acetamido, alpha-alkylmalonates. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 39 (1). pp. 10-15. ISSN 0376-4699
Full text not available from this repository.Abstract
Nine diethyl alpha-acetamido, alpha-alkylmalonates 3-11 (alkyl=methyl, benzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,6-difluorobenzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyl, 2-chlorobenzyl and 3-chlorobenzyl) have been synthesised in three steps starting with diethyl malonate in overall yields of 49-90%. The structures of C-alkylated acetamidomalonates have been established on the basis of their spectral data, the structures of two compounds 9 and 11 are also confirmed on the basis of their X-ray crystallographic studies. Further, the X-ray crystal structure of the chiral monoethyl ester of alpha-acetamidomalonic acid 1 has been studied. None of our C-alkylated acetamidomalonate has been found to be a substrate for lipase-catalysed enantiodifferentiating deesterification/ hydrolysis of the symmetric diester groups.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY |
| Publisher: | NATL INST SCIENCE COMMUNICATION |
| ISSN: | 0376-4699 |
| Date: | January 2000 |
| Volume: | 39 |
| Number: | 1 |
| Number of Pages: | 6 |
| Page Range: | pp. 10-15 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/13392 |
Data sourced from Thomson Reuters' Web of Knowledge
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