Literature DB >> 21861518

Biogenesis of the unique 4',5'-dehydronucleoside of the uridyl peptide antibiotic pacidamycin.

Amany E Ragab1, Sabine Grüschow, Daniel R Tromans, Rebecca J M Goss.   

Abstract

The pacidamycins belong to a class of antimicrobial nucleoside antibiotics that act by inhibiting the clinically unexploited target translocase I, a key enzyme in peptidoglycan assembly. As with other nucleoside antibiotics, the pacidamycin 4',5'-dehydronucleoside portion is an essential pharmacophore. Here we show that the biosynthesis of the pacidamycin nucleoside in Streptomyces coeruleorubidus proceeds through three steps from uridine. The transformations involve oxidation of the 5'-alcohol by Pac11, transamination of the resulting aldehyde by Pac5, and dehydration by the Cupin-domain protein Pac13.

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Year:  2011        PMID: 21861518     DOI: 10.1021/ja206163j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

1.  Archaeal Elp3 catalyzes tRNA wobble uridine modification at C5 via a radical mechanism.

Authors:  Kiruthika Selvadurai; Pei Wang; Joseph Seimetz; Raven H Huang
Journal:  Nat Chem Biol       Date:  2014-08-24       Impact factor: 15.040

Review 2.  Flavoenzymes: versatile catalysts in biosynthetic pathways.

Authors:  Christopher T Walsh; Timothy A Wencewicz
Journal:  Nat Prod Rep       Date:  2013-01       Impact factor: 13.423

3.  Fe(II)-dependent, uridine-5'-monophosphate α-ketoglutarate dioxygenases in the synthesis of 5'-modified nucleosides.

Authors:  Zhaoyong Yang; Jason Unrine; Koichi Nonaka; Steven G Van Lanen
Journal:  Methods Enzymol       Date:  2012       Impact factor: 1.600

Review 4.  Natural and engineered biosynthesis of nucleoside antibiotics in Actinomycetes.

Authors:  Wenqing Chen; Jianzhao Qi; Pan Wu; Dan Wan; Jin Liu; Xuan Feng; Zixin Deng
Journal:  J Ind Microbiol Biotechnol       Date:  2015-07-08       Impact factor: 3.346

Review 5.  Recent advances in the biosynthesis of nucleoside antibiotics.

Authors:  Taro Shiraishi; Tomohisa Kuzuyama
Journal:  J Antibiot (Tokyo)       Date:  2019-09-25       Impact factor: 2.649

Review 6.  Mechanism of action of nucleoside antibacterial natural product antibiotics.

Authors:  Timothy D H Bugg; Rachel V Kerr
Journal:  J Antibiot (Tokyo)       Date:  2019-08-30       Impact factor: 2.649

Review 7.  Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.

Authors:  M McErlean; X Liu; Z Cui; B Gust; S G Van Lanen
Journal:  Nat Prod Rep       Date:  2021-07-21       Impact factor: 15.111

8.  Pac13 is a Small, Monomeric Dehydratase that Mediates the Formation of the 3'-Deoxy Nucleoside of Pacidamycins.

Authors:  Freideriki Michailidou; Chun-Wa Chung; Murray J B Brown; Andrew F Bent; James H Naismith; William J Leavens; Sean M Lynn; Sunil V Sharma; Rebecca J M Goss
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-30       Impact factor: 15.336

9.  Sansanmycin natural product analogues as potent and selective anti-mycobacterials that inhibit lipid I biosynthesis.

Authors:  Anh T Tran; Emma E Watson; Venugopal Pujari; Trent Conroy; Luke J Dowman; Andrew M Giltrap; Angel Pang; Weng Ruh Wong; Roger G Linington; Sebabrata Mahapatra; Jessica Saunders; Susan A Charman; Nicholas P West; Timothy D H Bugg; Julie Tod; Christopher G Dowson; David I Roper; Dean C Crick; Warwick J Britton; Richard J Payne
Journal:  Nat Commun       Date:  2017-03-01       Impact factor: 14.919

10.  Flavoenzyme CrmK-mediated substrate recycling in caerulomycin biosynthesis.

Authors:  Yiguang Zhu; Marie-Ève Picard; Qingbo Zhang; Julie Barma; Xavier Murphy Després; Xiangui Mei; Liping Zhang; Jean-Baptiste Duvignaud; Manon Couture; Weiming Zhu; Rong Shi; Changsheng Zhang
Journal:  Chem Sci       Date:  2016-04-13       Impact factor: 9.825

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