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Title: Biosynthesis of the manumycin group antibiotics

Abstract

The biosynthesis of the manumycin group antibiotics manumycin (1) and asukamycin (2) was studied in Streptomyces parvulus Tue 64 and Streptomyces nodosus ssp. asukaensis ATCC 29,757 by using radioactive and stable isotope tracer techniques and high-field NMR spectroscopy. The results have demonstrated that the central, multifunctional mC{sub 7}N unit typical of this group of antibiotics, which serves as the starter unit for a short polyketide chain, is biosynthesized from a C{sub 4} Krebs cycle and a C{sub 3} triose phosphate pool intermediate by a new pathway, distinct from the shikimate, polyketide, or pentose phosphate routes leading to other mC{sub 7}N units in nature. The C{sub 5} unit in both 1 and 2 arises by a novel intramolecular cyclization of 5-aminolevulinic acid, and a cyclohexane ring and the adjacent carbon in 2 arise from the seven carbon atoms of shikimic acid. The side chains of both antibiotics represent typical polyketide-derived moieties, differing with respect to their combinations of starter and elongation units.

Authors:
;  [1]; ;  [2]; ;  [3]; ;  [4]
  1. Universitaet Goettingen (West Germany)
  2. Kitasato Univ., Tokyo (Japan)
  3. Ohio State Univ., Columbus (USA)
  4. Univ. of Washington, Seattle (USA)
Publication Date:
OSTI Identifier:
6793822
Resource Type:
Journal Article
Journal Name:
Journal of the American Chemical Society; (USA)
Additional Journal Information:
Journal Volume: 112:10; Journal ID: ISSN 0002-7863
Country of Publication:
United States
Language:
English
Subject:
62 RADIOLOGY AND NUCLEAR MEDICINE; ANTIBIOTICS; BIOSYNTHESIS; DATA ANALYSIS; EXPERIMENTAL DATA; MEASURING INSTRUMENTS; MEASURING METHODS; STABLE ISOTOPES; TRACER TECHNIQUES; ANTI-INFECTIVE AGENTS; DATA; DRUGS; INFORMATION; ISOTOPE APPLICATIONS; ISOTOPES; NUMERICAL DATA; SYNTHESIS; 550600* - Medicine

Citation Formats

Thiericke, R, Zeeck, A, Nakagawa, Akira, Omura, Satoshi, Herrold, R E, Wu, S T.S., Beale, J M, and Floss, H G. Biosynthesis of the manumycin group antibiotics. United States: N. p., 1990. Web. doi:10.1021/ja00166a039.
Thiericke, R, Zeeck, A, Nakagawa, Akira, Omura, Satoshi, Herrold, R E, Wu, S T.S., Beale, J M, & Floss, H G. Biosynthesis of the manumycin group antibiotics. United States. https://doi.org/10.1021/ja00166a039
Thiericke, R, Zeeck, A, Nakagawa, Akira, Omura, Satoshi, Herrold, R E, Wu, S T.S., Beale, J M, and Floss, H G. 1990. "Biosynthesis of the manumycin group antibiotics". United States. https://doi.org/10.1021/ja00166a039.
@article{osti_6793822,
title = {Biosynthesis of the manumycin group antibiotics},
author = {Thiericke, R and Zeeck, A and Nakagawa, Akira and Omura, Satoshi and Herrold, R E and Wu, S T.S. and Beale, J M and Floss, H G},
abstractNote = {The biosynthesis of the manumycin group antibiotics manumycin (1) and asukamycin (2) was studied in Streptomyces parvulus Tue 64 and Streptomyces nodosus ssp. asukaensis ATCC 29,757 by using radioactive and stable isotope tracer techniques and high-field NMR spectroscopy. The results have demonstrated that the central, multifunctional mC{sub 7}N unit typical of this group of antibiotics, which serves as the starter unit for a short polyketide chain, is biosynthesized from a C{sub 4} Krebs cycle and a C{sub 3} triose phosphate pool intermediate by a new pathway, distinct from the shikimate, polyketide, or pentose phosphate routes leading to other mC{sub 7}N units in nature. The C{sub 5} unit in both 1 and 2 arises by a novel intramolecular cyclization of 5-aminolevulinic acid, and a cyclohexane ring and the adjacent carbon in 2 arise from the seven carbon atoms of shikimic acid. The side chains of both antibiotics represent typical polyketide-derived moieties, differing with respect to their combinations of starter and elongation units.},
doi = {10.1021/ja00166a039},
url = {https://www.osti.gov/biblio/6793822}, journal = {Journal of the American Chemical Society; (USA)},
issn = {0002-7863},
number = ,
volume = 112:10,
place = {United States},
year = {Wed May 09 00:00:00 EDT 1990},
month = {Wed May 09 00:00:00 EDT 1990}
}