SYNTHESIS OF STEREOSPECIFICALLY LABELED D-PROP-2-YNYLGLYCINE AND INVESTIGATION OF THE ACTION OF D-AMINO-ACID OXIDASE

被引：15

作者：

CHURCH, NJ ^{[1
]}

YOUNG, DW ^{[1
]}

机构：

[1] UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 08期

关键词：

D O I：

10.1039/c39940000943

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereospecifically deuteriated samples of D-prop-2-ynylglycine 1 are synthesised by reaction of the labelled aziridines 13 with a carbon nucleophile followed by deprotection; incubation of these samples with D-amino acid oxidase indicates that, in formation of the lactone 5, deprotonation at C-3 is non-stereospecific, strongly supporting non-enzymatic deprotonation as a key step in the formation of this compound.

引用

页码：943 / 944

页数：2

共 8 条

[1] VERSATILE SYNTHESIS OF STEREOSPECIFICALLY LABELED D-AMINO ACIDS VIA LABELED AZIRIDINES - PREPARATION OF (2R,3S)-[3-H-2(1)]-SERINE AND (2R,3R)-[2,3-H-2(2)]-SERINE (2S,2'S,3S,3'S-[3,3'-H-2(2)]-CYSTINE AND (2S,2'S,3R,3'R)-[2,2',3,3'-H-2(4)]-CYSTINE AND (2S,3S)-[3-H-2(1)-] AND (2S,3R)-[2,3-H-2(2)]-BETA-CHLOROALANINE
AXELSSON, BS
OTOOLE, KJ
SPENCER, PA
YOUNG, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (07): : 807 - 815
[2] A VERSATILE SYNTHESIS OF STEREOSPECIFICALLY LABELED D-AMINO ACIDS AND RELATED ENZYME-INHIBITORS
AXELSSON, BS
OTOOLE, KJ
SPENCER, PA
YOUNG, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) : 1085 - 1086
[3] NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS
BALDWIN, JE
ADLINGTON, RM
ROBINSON, NG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) : 153 - 155
[4] AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
BALDWIN, JE
SPIVEY, AC
SCHOFIELD, CJ
SWEENEY, JB
[J]. TETRAHEDRON, 1993, 49 (28) : 6309 - 6330
[5] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
BALDWIN, JE
ADLINGTON, RM
ONEIL, IA
SCHOFIELD, C
SPIVEY, AC
SWEENEY, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1852 - 1854
[6] SEQUENCE OF REACTIONS WHICH FOLLOWS ENZYMATIC OXIDATION OF PROPARGYLGLYCINE
MARCOTTE, P
WALSH, C
[J]. BIOCHEMISTRY, 1978, 17 (26) : 5613 - 5619
[7] VINYLGLYCINE AND PROPARGYLGLYCINE - COMPLEMENTARY SUICIDE SUBSTRATES FOR L-AMINO-ACID OXIDASE AND D-AMINO-ACID OXIDASE
MARCOTTE, P
WALSH, C
[J]. BIOCHEMISTRY, 1976, 15 (14) : 3070 - 3076
[8] AN ACID LABILE ARGININE DERIVATIVE FOR PEPTIDE-SYNTHESIS - N(G)-2,2,5,7,8-PENTAMETHYLCHROMAN-6-SULFONYL-L-ARGININE
RAMAGE, R
GREEN, J
BLAKE, AJ
[J]. TETRAHEDRON, 1991, 47 (32) : 6353 - 6370

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