Literature DB >> 15606070

Modular synthesis of pantetheine and phosphopantetheine.

Alexander L Mandel1, James J La Clair, Michael D Burkart.   

Abstract

[structure: see text] D-Pantetheine and D-phosphopantetheine, precursors to coenzyme A, have been synthesized though a linear sequence from three modules (M1-M3) in 9 and 10 steps, respectively. These routes provide access to analogues of coenzyme A containing modified cystamines, beta-alanines, and pantoic acid residues. All three modules were joined using conventional methods of peptide synthesis. The chiral component, M3, was derived from D-pantolactone.

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Year:  2004        PMID: 15606070     DOI: 10.1021/ol048853+

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  15 in total

1.  Discovery of inhibitors of 4'-phosphopantetheine adenylyltransferase (PPAT) to validate PPAT as a target for antibacterial therapy.

Authors:  Boudewijn L M de Jonge; Grant K Walkup; Sushmita D Lahiri; Hoan Huynh; Georg Neckermann; Luke Utley; Tory J Nash; Jesse Brock; Maryann San Martin; Amy Kutschke; Michele Johnstone; Valerie Laganas; Laurel Hajec; Rong-Fang Gu; Haihong Ni; Brendan Chen; Kim Hutchings; Elise Holt; David McKinney; Ning Gao; Stephania Livchak; Jason Thresher
Journal:  Antimicrob Agents Chemother       Date:  2013-09-16       Impact factor: 5.191

2.  Synthesis of 4'-aminopantetheine and derivatives to probe aminoglycoside N-6'-acetyltransferase.

Authors:  Xuxu Yan; T Olukayode Akinnusi; Aaron T Larsen; Karine Auclair
Journal:  Org Biomol Chem       Date:  2011-01-12       Impact factor: 3.876

3.  Reaction intermediate analogues as bisubstrate inhibitors of pantothenate synthetase.

Authors:  Zhixiang Xu; Wei Yin; Leonardo K Martinelli; Joanna Evans; Jinglei Chen; Yang Yu; Daniel J Wilson; Valerie Mizrahi; Chunhua Qiao; Courtney C Aldrich
Journal:  Bioorg Med Chem       Date:  2014-01-23       Impact factor: 3.641

4.  Geminal dialkyl derivatives of N-substituted pantothenamides: synthesis and antibacterial activity.

Authors:  T Olukayode Akinnusi; Kenward Vong; Karine Auclair
Journal:  Bioorg Med Chem       Date:  2011-03-04       Impact factor: 3.641

Review 5.  Using modern tools to probe the structure-function relationship of fatty acid synthases.

Authors:  Kara Finzel; D John Lee; Michael D Burkart
Journal:  Chembiochem       Date:  2015-02-10       Impact factor: 3.164

6.  Exploring structural motifs necessary for substrate binding in the active site of Escherichia coli pantothenate kinase.

Authors:  Emelia Awuah; Eric Ma; Annabelle Hoegl; Kenward Vong; Eric Habib; Karine Auclair
Journal:  Bioorg Med Chem       Date:  2014-04-24       Impact factor: 3.641

7.  Modular synthesis of cell-permeating 2-ketoglutarate esters.

Authors:  Thomas T Zengeya; Rhushikesh A Kulkarni; Jordan L Meier
Journal:  Org Lett       Date:  2015-04-27       Impact factor: 6.005

8.  Four enzymes define the incorporation of coenzyme A in thienamycin biosynthesis.

Authors:  Michael F Freeman; Kristos A Moshos; Micah J Bodner; Rongfeng Li; Craig A Townsend
Journal:  Proc Natl Acad Sci U S A       Date:  2008-08-04       Impact factor: 11.205

9.  Metabolic perturbation of an essential pathway: evaluation of a glycine precursor of coenzyme A.

Authors:  Michael Rothmann; MinJin Kang; Reymundo Villa; Ioanna Ntai; James J La Clair; Neil L Kelleher; Eli Chapman; Michael D Burkart
Journal:  J Am Chem Soc       Date:  2013-04-10       Impact factor: 15.419

10.  A detailed biochemical characterization of phosphopantothenate synthetase, a novel enzyme involved in coenzyme A biosynthesis in the Archaea.

Authors:  Takuya Ishibashi; Hiroya Tomita; Yuusuke Yokooji; Tatsuya Morikita; Bunta Watanabe; Jun Hiratake; Asako Kishimoto; Akiko Kita; Kunio Miki; Tadayuki Imanaka; Haruyuki Atomi
Journal:  Extremophiles       Date:  2012-09-02       Impact factor: 2.395

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