Moenomycin A: New chemistry that allows to attach the antibiotic to reporter groups, solid supports, and proteins

被引:21
作者
Kempin, U
Hennig, L
Knoll, D
Welzel, P
Muller, D
Markus, A
vanHeijenoort, J
机构
[1] UNIV LEIPZIG,INST ORGAN CHEM,D-04103 LEIPZIG,GERMANY
[2] RUHR UNIV BOCHUM,FAK CHEM,D-44780 BOCHUM,GERMANY
[3] HOECHST MAR ROUSSEL,D-65926 FRANKFURT,GERMANY
[4] UNIV PARIS 11,F-91405 ORSAY,FRANCE
关键词
D O I
10.1016/S0040-4020(97)10234-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Moenomycin A (18) on reaction with the diazonium salt derived from bifunctional (protected) 15 yields the coupling product 19 which on reduction is converted into the moenomycin thiol derivative 21. Thiol 21 has been used to prepare selectively moenomycin dansyl and biotin adducts 26 and 28, respectively. This work was performed with the aim to use moenomycin as a tool for studies of the transglycosylation step in peptidoglycan biosynthesis. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:17669 / 17690
页数:22
相关论文
共 43 条
[1]  
AKHREM AA, 1976, KHIM GETEROTSIKL, V5, P625
[2]  
CANONICA L, 1966, TETRAHEDRON LETT, V26, P3031
[3]  
CORBELLA A, 1965, CHIM ITAL, V95, P948
[4]   THIOL-REACTIVE FLUORESCENT-PROBES FOR PROTEIN LABELING [J].
CORRIE, JET .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (20) :2975-2982
[5]   A STRUCTURALLY AND BIOGENETICALLY INTERESTING MOENOMYCIN ANTIBIOTIC [J].
DONNERSTAG, A ;
MARZIAN, S ;
MULLER, D ;
WELZEL, P ;
BOTTGER, D ;
STARK, A ;
FEHLHABER, HW ;
MARKUS, A ;
VANHEIJENOORT, Y ;
VANHEIJENOORT, J .
TETRAHEDRON, 1995, 51 (07) :1931-1940
[6]   COLABOMYCIN CO-METABOLITES - SYNTHESIS OF 2880-II, A METABOLITE RELATED TO FERULIC ACID [J].
EBENEZER, WJ .
SYNTHETIC COMMUNICATIONS, 1991, 21 (03) :351-358
[7]  
EISTERT B, 1963, LIEBIGS ANN CHEM, V666, P97
[8]   SERINE BETA-LACTAMASES AND PENICILLIN-BINDING PROTEINS [J].
GHUYSEN, JM .
ANNUAL REVIEW OF MICROBIOLOGY, 1991, 45 :37-67
[9]  
Hatanaka Y, 1996, CARBOHYD RES, V294, P95
[10]   Fluorescent cyclodextrins for molecule sensing: Fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins [J].
Ikeda, H ;
Nakamura, M ;
Ise, N ;
Oguma, N ;
Nakamura, A ;
Ikeda, T ;
Toda, F ;
Ueno, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :10980-10988