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Literature DB >> 22296295

Synthesis of the AviMeCys-containing D-ring of mersacidin.

Angela K Carrillo¹, Michael S VanNieuwenhze.

Abstract

A chemical synthesis of the D-ring of mersacidin is reported. The synthetic route relied upon development of a method for late-stage introduction of an unusual S-[(Z)-2-aminovinyl]-(3S)-3-methyl-D-cysteine (AviMeCys) functional group via an oxidative decarbonylation/decarboxylation reaction.

Entities: Chemical Species

Mesh：

Substances：

Year: 2012 PMID： 22296295 PMCID： PMC4096711 DOI： 10.1021/ol2034806

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

19 in total

1. The flavoprotein MrsD catalyzes the oxidative decarboxylation reaction involved in formation of the peptidoglycan biosynthesis inhibitor mersacidin.

Authors: Florian Majer; Dietmar G Schmid; Karsten Altena; Gabriele Bierbaum; Thomas Kupke
Journal: J Bacteriol Date: 2002-03 Impact factor: 3.490

Review 2. Biosynthesis and mode of action of lantibiotics.

Authors: Champak Chatterjee; Moushumi Paul; Lili Xie; Wilfred A van der Donk
Journal: Chem Rev Date: 2005-02 Impact factor: 60.622

3. A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide.

Authors: K C Nicolaou; Anthony A Estrada; Mark Zak; Sang Hyup Lee; Brian S Safina
Journal: Angew Chem Int Ed Engl Date: 2005-02-18 Impact factor: 15.336

4. 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.

Authors: H Li; X Jiang; Y H Ye; C Fan; T Romoff; M Goodman
Journal: Org Lett Date: 1999-07-15 Impact factor: 6.005

5. Versatile and stereoselective syntheses of orthogonally protected beta-methylcysteine and beta-methyllanthionine.

Authors: Radha S Narayan; Michael S Vannieuwenhze
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

6. The lantibiotic mersacidin inhibits peptidoglycan biosynthesis at the level of transglycosylation.

Authors: H Brötz; G Bierbaum; P E Reynolds; H G Sahl
Journal: Eur J Biochem Date: 1997-05-15

7. The lantibiotic mersacidin inhibits peptidoglycan synthesis by targeting lipid II.

Authors: H Brötz; G Bierbaum; K Leopold; P E Reynolds; H G Sahl
Journal: Antimicrob Agents Chemother Date: 1998-01 Impact factor: 5.191

8. Construction of an expression system for site-directed mutagenesis of the lantibiotic mersacidin.

Authors: Christiane Szekat; Ralph W Jack; Dirk Skutlarek; Harald Färber; Gabriele Bierbaum
Journal: Appl Environ Microbiol Date: 2003-07 Impact factor: 4.792

9. NMR study of mersacidin and lipid II interaction in dodecylphosphocholine micelles. Conformational changes are a key to antimicrobial activity.

Authors: Shang-Te D Hsu; Eefjan Breukink; Gabriele Bierbaum; Hans-Georg Sahl; Ben de Kruijff; Rob Kaptein; Nico A J van Nuland; Alexandre M J J Bonvin
Journal: J Biol Chem Date: 2003-01-31 Impact factor: 5.157

Synthesis of the AviMeCys-containing D-ring of mersacidin.

1. The flavoprotein MrsD catalyzes the oxidative decarboxylation reaction involved in formation of the peptidoglycan biosynthesis inhibitor mersacidin.

Review 2. Biosynthesis and mode of action of lantibiotics.

3. A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide.

4. 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.

5. Versatile and stereoselective syntheses of orthogonally protected beta-methylcysteine and beta-methyllanthionine.

6. The lantibiotic mersacidin inhibits peptidoglycan biosynthesis at the level of transglycosylation.

7. The lantibiotic mersacidin inhibits peptidoglycan synthesis by targeting lipid II.

8. Construction of an expression system for site-directed mutagenesis of the lantibiotic mersacidin.

9. NMR study of mersacidin and lipid II interaction in dodecylphosphocholine micelles. Conformational changes are a key to antimicrobial activity.

10. Mode of action of the lantibiotic mersacidin: inhibition of peptidoglycan biosynthesis via a novel mechanism?

1. Carboxyl Analogue of Mutacin 1140, a Scaffold for Lead Antibacterial Discovery.

2. Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

3. Synthesis and Bioactivity of Diastereomers of the Virulence Lanthipeptide Cytolysin.

4. Chemical synthesis and biological activity of analogues of the lantibiotic epilancin 15X.

5. New charge-bearing amino acid residues that promote β-sheet secondary structure.

6. Mutational Studies of the Mersacidin Leader Reveal the Function of Its Unique Two-Step Leader Processing Mechanism.

7. Chemical synthesis of the lantibiotic lacticin 481 reveals the importance of lanthionine stereochemistry.