Biosynthesis of 4-aminoheptose 2-epimers, core structural components of the septacidins and spicamycins.
J Antibiot (Tokyo)
; 67(5): 405-14, 2014 May.
Article
em En
| MEDLINE
| ID: mdl-24643053
ABSTRACT
Septacidins and spicamycins are acylated 4-aminoheptosyl-ß-N-glycosides produced by Streptomyces fimbriatus and S. alanosinicus, respectively. Their structures are highly conserved, but differ in the stereochemistry of the 4-aminoheptosyl residues. The origin of this stereochemistry is unknown, but is presumably because of the difference in their biosynthetic pathways. We have synthesized the septacidin 4-aminoheptose to verify the difference between septacidin and spicamycin. Isotopic enrichment studies were undertaken using S. fimbriatus, and show that the septacidin heptose is derived from the pentose phosphate pathway. This indicates conserved pathways leading to the biosynthesis of 4-amino-4-deoxy-L-gluco-heptose or 4-amino-4-deoxy-L-manno-heptose.
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MEDLINE
Assunto principal:
Antibióticos Antineoplásicos
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article