SYNTHESIS OF DELTA-L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-ALLYLGLYCINE, AND 8 DEUTERATED ANALOGS, SUBSTRATES FOR THE INVESTIGATION OF THE MECHANISM OF ACTION OF ISOPENICILLIN-N SYNTHASE

被引:14
作者
BALDWIN, JE [1 ]
BRADLEY, M [1 ]
TURNER, NJ [1 ]
ADLINGTON, RM [1 ]
PITT, AR [1 ]
SHERIDAN, H [1 ]
机构
[1] UNIV OXFORD,OXFORD CTR MOLEC SCI,OXFORD OX1 3QY,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)91015-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine (1a) from its component amino acids is described, along with the synthesis of eight analogues (1b-i) specifically deuterated at C-3 and/or C-5 of the allylglycine residue.
引用
收藏
页码:8203 / 8222
页数:20
相关论文
共 24 条
[1]   AMINO-ACIDS AND PEPTIDES .2. NEW METHOD FOR PREPARING DIAZODIPHENYLMETHANE AND RELATED COMPOUNDS [J].
ADAMSON, JR ;
BYWOOD, R ;
EASTLICK, DT ;
GALLAGHER, G ;
WALKER, D ;
WILSON, EM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (20) :2030-2033
[2]  
ADLINGTON RM, 1984, TETRAHEDRON, V40, P1907
[3]   A NEW METHOD FOR THE PROTECTION OF THE SULFHYDRYL GROUP DURING PEPTIDE SYNTHESIS [J].
AKABORI, S ;
SAKAKIBARA, S ;
SHIMONISHI, Y ;
NOBUHARA, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1964, 37 (03) :433-434
[4]  
BALDWIN JE, 1984, J CHEM SOC CHEM COMM, P984, DOI 10.1039/c39840000984
[5]   SYNTHESIS OF DELTA-(L-ALPHA-AMINOADIPOYL)-L-CYSTEINYL-D-VALINE AND SOME C-13 AND N-15 LABELED ISOTOPOMERS [J].
BALDWIN, JE ;
HERCHEN, SR ;
JOHNSON, BL ;
JUNG, M ;
USHER, JJ ;
WAN, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08) :2253-2257
[6]   EVIDENCE FOR EPOXIDE FORMATION FROM ISOPENICILLIN-N SYNTHASE [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BRADLEY, M ;
TURNER, NJ ;
PITT, AR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (15) :978-981
[7]   PENICILLIN BIOSYNTHESIS - MULTIPLE PATHWAYS FROM A MODIFIED SUBSTRATE [J].
BALDWIN, JE ;
ADLINGTON, RM ;
DEROME, AE ;
TING, HH ;
TURNER, NJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1211-1214
[8]  
BALDWIN JE, 1988, J CHEM SOC CHEM COMM, P1126
[9]  
BALDWIN JE, 1979, BIOCHEM J, V184, P427
[10]   ESTER-ENOLATE CLAISEN REARRANGEMENT OF ALPHA-AMINO-ACID DERIVATIVES [J].
BARTLETT, PA ;
BARSTOW, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3933-3941