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Titolo:
CHEMISTRY AND STRUCTURE OF GANEFROMYCIN
Autore:
CARTER GT; PHILLIPSON DW; WEST RR; BORDERS DB;
Indirizzi:
AMER CYANAMID CO,LEDERLE LABS,DIV MED RES PEARL RIVER NY 10965
Titolo Testata:
Journal of organic chemistry
fascicolo: 24, volume: 58, anno: 1993,
pagine: 6588 - 6595
SICI:
0022-3263(1993)58:24<6588:CASOG>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
BIOLOGICAL-ACTIVITY; EFROTOMYCIN FAMILY; ANTIBIOTICS; LL-E19020-ALPHA; MEMBER;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
14
Recensione:
Indirizzi per estratti:
Citazione:
G.T. Carter et al., "CHEMISTRY AND STRUCTURE OF GANEFROMYCIN", Journal of organic chemistry, 58(24), 1993, pp. 6588-6595

Abstract

Ganefromycins are antibiotics produced by Streptomyces lydicus sp. tanzanius having commercial potential as performance enhancement agents for livestock. Ganefromycins are related to the elfamycin family of antibiotics but contain several unique chemical features which are the source of novel and unexpected chemistry. Reactions under mildly basic conditions resulted in the interconversion of ganefromycins alpha (1) and beta (2) by a 1,2-acyl migration. Strong base causes elimination of a trisaccharide whose structure was solved by single-crystal X-ray diffraction analysis of the triacetate of the reduced ring-opened triol. Ammonolysis yields the same rearranged product from either 1 or 2. Evidence is provided for the mechanism of this rearrangement involving elimination of the saccharide to form a transient alpha,beta-unsaturated carbonyl, Michael addition of ammonia, and intramolecular transacylation. Ozonolysis and acidic methanolysis were employed to obtain simplified compounds for structure determination. Ganefromycin beta fragments in warm acetic acid solution, releasing the long-chain amino acid. C-13 NMR data with assignments are provided for the degradation products.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 03:30:41