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Title: Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl α-acetamido, α-alkylmalonates
Authors: Singh, Amarjit
Prasad, Ashok K
Errington, William
Belokon, Yuri N
Kochetkov, Konstantine A
Saxena, Rajendra K
Jain, Subhash C
Parmar, Virinder S
Issue Date: Jan-2000
Publisher: NISCAIR-CSIR, India
Abstract: Nine diethyl α-acetamido, α-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 α-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.
Page(s): 10-15
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.39B(01) [January 2000]

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