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
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
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页码:943 / 944
页数:2
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[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 [J].
AXELSSON, BS ;
OTOOLE, KJ ;
SPENCER, PA ;
YOUNG, DW .
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 [J].
AXELSSON, BS ;
OTOOLE, KJ ;
SPENCER, PA ;
YOUNG, DW .
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 [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ROBINSON, NG .
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 [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ ;
SWEENEY, JB .
TETRAHEDRON, 1993, 49 (28) :6309-6330
[5]   THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ONEIL, IA ;
SCHOFIELD, C ;
SPIVEY, AC ;
SWEENEY, JB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1852-1854
[6]   SEQUENCE OF REACTIONS WHICH FOLLOWS ENZYMATIC OXIDATION OF PROPARGYLGLYCINE [J].
MARCOTTE, P ;
WALSH, C .
BIOCHEMISTRY, 1978, 17 (26) :5613-5619
[7]   VINYLGLYCINE AND PROPARGYLGLYCINE - COMPLEMENTARY SUICIDE SUBSTRATES FOR L-AMINO-ACID OXIDASE AND D-AMINO-ACID OXIDASE [J].
MARCOTTE, P ;
WALSH, C .
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 [J].
RAMAGE, R ;
GREEN, J ;
BLAKE, AJ .
TETRAHEDRON, 1991, 47 (32) :6353-6370