Literature DB >> 11918068

Biosynthesis of hibarimicins. III. Structures of new hibarimicin-related metabolites produced by blocked mutants.

Yasuhiro Igarashi1, Takayuki Kajiura, Tamotsu Furumai, Hiroshi Hori, Kazuaki Higashi, Tadayuki Ishiyama, Masakazu Uramoto, Yoshimasa Uehara, Toshikazu Oki.   

Abstract

Structures of metabolites produced by blocked mutants of Microbispora rosea subsp. hibaria TP-A0121, hibarimicin-producer, were determined by spectroscopic analysis. HMP-Y6 is the dimer of the west half of hibarimicin B, the aglycon of which is the genuine biosynthetic intermediate. HMP-P1 is the shunt product arising from the release of a methanol molecule from hibarimicinone. HMP-P4, the glycoside of HMP-P1, is glycosylated with two amicetoses and two digitoxoses same as hibarimicin B. HMP-M1, M2, M3 and M4 are shunt products derived from the monomeric undecaketide intermediates.

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Year:  2002        PMID: 11918068     DOI: 10.7164/antibiotics.55.61

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  7 in total

1.  Assignment and stereocontrol of hibarimicin atropoisomers.

Authors:  Ian M Romaine; Jonathan E Hempel; Ganesh Shanmugam; Hiroshi Hori; Yasuhiro Igarashi; Prasad L Polavarapu; Gary A Sulikowski
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

Review 2.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

3.  Total syntheses of HMP-Y1, hibarimicinone, and HMP-P1.

Authors:  Brian B Liau; Benjamin C Milgram; Matthew D Shair
Journal:  J Am Chem Soc       Date:  2012-09-26       Impact factor: 15.419

4.  Synthesis of an A'B' Precursor to Angelmicin B: Product Diversification in the Suárez Lactol Fragmentation.

Authors:  Jialiang Li; Louis Todaro; David R Mootoo
Journal:  European J Org Chem       Date:  2011-09-07

5.  Gram-scale synthesis of the A'B'-subunit of angelmicin B.

Authors:  Benjamin C Milgram; Brian B Liau; Matthew D Shair
Journal:  Org Lett       Date:  2011-11-15       Impact factor: 6.005

6.  Studies on a biomimetic oxidative dimerization approach to the hibarimicins.

Authors:  Ian M Romaine; Gary A Sulikowski
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

7.  Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence.

Authors:  Jialiang Li; Louis J Todaro; David R Mootoo
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005

  7 in total

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