Synthesis of optically pure alpha-hydroxyglycine peptides

被引:11
作者
Bogenstatter, M [1 ]
Steglich, W [1 ]
机构
[1] UNIV MUNICH,INST ORGAN CHEM,D-80333 MUNICH,GERMANY
关键词
C-TERMINAL AMIDE; AMIDATING MONOOXYGENASE; EXTENDED PEPTIDES; DERIVATIVES; ENZYME; ACID; STEREOCHEMISTRY; AMIDOALKYLATION; BIOSYNTHESIS; INTERMEDIATE;
D O I
10.1016/S0040-4020(97)00429-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically pure alpha-hydroxyglycine peptides can be prepared by enzymatic resolution of DL-alpha-(benzyloxy)glycine peptide esters with subtilisin Carlsberg followed by hydrogenolysis of the benzyl protecting group. The DL-alpha-(benzyloxy)glycine peptide esters were obtained from the corresponding serine derivatives via lead tetraacetate oxidation and reaction of the resulting electrophilic glycine equivalents with benzyl alcohol. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7267 / 7274
页数:8
相关论文
共 32 条
[31]   INCORPORATION OF AEROBIC OXYGEN INTO THE HYDROXYGLYCYL INTERMEDIATE DURING FORMATION OF C-TERMINAL PEPTIDE AMIDES BY PEPTIDYLGLYCINE ALPHA-AMIDATING MONOOXYGENASE (PAM) [J].
ZABRISKIE, TM ;
CHENG, HM ;
VEDERAS, JC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (08) :571-572
[32]   AMIDOALKYLATION OF MERCAPTANS WITH GLYOXYLIC-ACID DERIVATIVES [J].
ZOLLER, U ;
BENISHAI, D .
TETRAHEDRON, 1975, 31 (07) :863-866