ENZYMATIC CONVERSION OF DEUTERATED ANALOGS OF DELTA-L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-ALLYLGLYCINE, AN UNNATURAL SUBSTRATE FOR ISOPENICILLIN N SYNTHASE - A UNIFIED THEORY OF 2ND RING-CLOSURE

被引:7
作者
BALDWIN, JE [1 ]
BRADLEY, M [1 ]
TURNER, NJ [1 ]
ADLINGTON, RM [1 ]
PITT, AR [1 ]
DEROME, AE [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)91016-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enzyme Isopenicillin N Synthase catalyses the conversion of the modified substrate delta-L-alpha-aminoadipoyl-L-cysteinyl-D-allylglycine to six beta-lactam containing metabolites. Eight tripeptides deuterated in the allylglycine moiety have been prepared and the stereochemical course of their cyclization to the beta-lactam containing metabolites has been investigated.
引用
收藏
页码:8223 / 8242
页数:20
相关论文
共 23 条
[1]   USE OF THE CYCLOPROPYLCARBINYL TEST TO DETECT A RADICAL-LIKE INTERMEDIATE IN PENICILLIN BIOSYNTHESIS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
DOMAYNEHAYMAN, BP ;
KNIGHT, G ;
TING, HH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1661-1663
[2]  
BALDWIN JE, 1984, J CHEM SOC CHEM COMM, P984, DOI 10.1039/c39840000984
[3]   PENICILLIN BIOSYNTHESIS - MODEL FOR CARBON-SULFUR BOND FORMATION [J].
BALDWIN, JE ;
WAN, TS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (06) :249-250
[4]   PENICILLIN BIOSYNTHESIS - DUAL PATHWAYS FROM A MODIFIED SUBSTRATE [J].
BALDWIN, JE ;
ABRAHAM, EP ;
ADLINGTON, RM ;
CHAKRAVARTI, B ;
DEROME, AE ;
MURPHY, JA ;
FIELD, LD ;
GREEN, NB ;
TING, HH ;
USHER, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (22) :1317-1319
[5]   PENICILLIN BIOSYNTHESIS - ON THE STEREOCHEMISTRY OF CARBON-SULFUR BOND FORMATION WITH MODIFIED SUBSTRATES [J].
BALDWIN, JE ;
ABRAHAM, EP ;
ADLINGTON, RM ;
MURPHY, JA ;
GREEN, NB ;
TING, HH ;
USHER, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (22) :1319-1320
[6]   PENICILLIN BIOSYNTHESIS - STEREOCHEMISTRY OF DESATURATIVE AND HYDROXYLATIVE PATHWAYS FROM L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-ISODEHYDROVALINE WITH ISOPENICILLIN-N SYNTHASE [J].
BALDWIN, JE ;
ADLINGTON, RM ;
KING, LG ;
PARISI, MF ;
SOBEY, WJ ;
SUTHERLAND, JD ;
TING, HH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (24) :1635-1637
[7]   THE BIOSYNTHESIS OF PENICILLINS AND CEPHALOSPORINS [J].
BALDWIN, JE ;
ABRAHAM, E .
NATURAL PRODUCT REPORTS, 1988, 5 (02) :129-145
[8]   PENICILLIN BIOSYNTHESIS - THE ORIGIN OF HYDROXY-GROUPS IN BETA-LACTAMS DERIVED FROM UNSATURATED SUBSTRATES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
FLITSCH, SL ;
TING, HH ;
TURNER, NJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (17) :1305-1308
[9]   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
[10]   PURIFICATION AND CHARACTERIZATION OF CLONED ISOPENICILLIN-N SYNTHETASE [J].
BALDWIN, JE ;
KILLIN, SJ ;
PRATT, AJ ;
SUTHERLAND, JD ;
TURNER, NJ ;
CRABBE, MJC ;
ABRAHAM, EP ;
WILLIS, AC .
JOURNAL OF ANTIBIOTICS, 1987, 40 (05) :652-659