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J Antibiot (Tokyo). 2014 May;67(5):405-14. doi: 10.1038/ja.2014.15. Epub 2014 Mar 19.

Biosynthesis of 4-aminoheptose 2-epimers, core structural components of the septacidins and spicamycins.

Author information

1
USDA-ARS, National Center for Agricultural Utilization Research, Peoria, IL, USA.
2
Department of Chemistry, Wayne State University, Detroit, MI, USA.
3
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, China.

Abstract

Septacidins and spicamycins are acylated 4-aminoheptosyl-β-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.

PMID:
24643053
DOI:
10.1038/ja.2014.15
[Indexed for MEDLINE]
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