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Literature DB >> 17061868

Degradation and reconstruction of moenomycin A and derivatives: dissecting the function of the isoprenoid chain.

Masaatsu Adachi¹, Yi Zhang, Catherine Leimkuhler, Binyuan Sun, John V LaTour, Daniel E Kahne.

Abstract

Moenomycin A is the only known natural product that inhibits peptidoglycan biosynthesis by binding the bacterial transglycosylases. We describe a degradation/reconstruction route to manipulate the reducing end of moenomycin A. A comparison of the biological and enzyme inhibitory activity of moenomycin A and an analogue containing a nerol lipid in place of the natural C25 lipid chain provides insight into the role of the moenocinol unit. Our results show that a lipid chain having ten carbons in moenocinol is sufficient for enzyme inhibition, but a longer chain is required for biological acitivity, apparently because the molecule must partition into biological membranes to reach its target in bacterial cells.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17061868 PMCID： PMC3197780 DOI： 10.1021/ja065905c

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

7 in total

Review 1. Syntheses around the transglycosylation step in peptidoglycan biosynthesis.

Authors: Peter Welzel
Journal: Chem Rev Date: 2005-12 Impact factor: 60.622

Review 2. Formation of the glycan chains in the synthesis of bacterial peptidoglycan.

Authors: J van Heijenoort
Journal: Glycobiology Date: 2001-03 Impact factor: 4.313

Review 3. Inhibition of transglycosylation involved in bacterial peptidoglycan synthesis.

Authors: R C Goldman; D Gange
Journal: Curr Med Chem Date: 2000-08 Impact factor: 4.530

4. Isolation and analysis of moenomycin and its biosynthetic intermediates from Streptomyces ghanaensis (ATCC 14672) wildtype and selected mutants.

Authors: B Subramaniam-Niehaus; T Schneider; J W Metzger; W Wohlleben
Journal: Z Naturforsch C J Biosci Date: 1997 Mar-Apr

5. Characterisation of antibiotic moenomycin A interaction with phospholipid model membranes.

Authors: F Volke; R Waschipky; A Pampel; A Donnerstag; G Lantzsch; H Pfeiffer; W Richter; G Klose; P Welzel
Journal: Chem Phys Lipids Date: 1997-02-28 Impact factor: 3.329

6. Kinetic characterization of the glycosyltransferase module of Staphylococcus aureus PBP2.

Authors: Dianah Barrett; Catherine Leimkuhler; Lan Chen; Deborah Walker; Daniel Kahne; Suzanne Walker
Journal: J Bacteriol Date: 2005-03 Impact factor: 3.490

7. Differential inhibition of Staphylococcus aureus PBP2 by glycopeptide antibiotics.

Authors: Catherine Leimkuhler; Lan Chen; Dianah Barrett; Gianbattista Panzone; Binyuan Sun; Brian Falcone; Markus Oberthür; Stefano Donadio; Suzanne Walker; Daniel Kahne
Journal: J Am Chem Soc Date: 2005-03-16 Impact factor: 15.419

7 in total

17 in total

Review 1. Moenomycin family antibiotics: chemical synthesis, biosynthesis, and biological activity.

Authors: Bohdan Ostash; Suzanne Walker
Journal: Nat Prod Rep Date: 2010-08-23 Impact factor: 13.423

2. A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

Authors: David E White; Pamela M Tadross; Zhe Lu; Eric N Jacobsen
Journal: Tetrahedron Date: 2014-07-08 Impact factor: 2.457

3. Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics.

Authors: Christian M Gampe; Hirokazu Tsukamoto; Tsung-Shing Andrew Wang; Suzanne Walker; Daniel Kahne
Journal: Tetrahedron Date: 2011-12-23 Impact factor: 2.457

4. Moenomycin resistance mutations in Staphylococcus aureus reduce peptidoglycan chain length and cause aberrant cell division.

Authors: Yuriy Rebets; Tania Lupoli; Yuan Qiao; Kathrin Schirner; Regis Villet; David Hooper; Daniel Kahne; Suzanne Walker
Journal: ACS Chem Biol Date: 2013-11-20 Impact factor: 5.100

Degradation and reconstruction of moenomycin A and derivatives: dissecting the function of the isoprenoid chain.

Review 1. Syntheses around the transglycosylation step in peptidoglycan biosynthesis.

Review 2. Formation of the glycan chains in the synthesis of bacterial peptidoglycan.

Review 3. Inhibition of transglycosylation involved in bacterial peptidoglycan synthesis.

4. Isolation and analysis of moenomycin and its biosynthetic intermediates from Streptomyces ghanaensis (ATCC 14672) wildtype and selected mutants.

5. Characterisation of antibiotic moenomycin A interaction with phospholipid model membranes.

6. Kinetic characterization of the glycosyltransferase module of Staphylococcus aureus PBP2.

7. Differential inhibition of Staphylococcus aureus PBP2 by glycopeptide antibiotics.

Review 1. Moenomycin family antibiotics: chemical synthesis, biosynthesis, and biological activity.

2. A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

3. Modular synthesis of diphospholipid oligosaccharide fragments of the bacterial cell wall and their use to study the mechanism of moenomycin and other antibiotics.

4. Moenomycin resistance mutations in Staphylococcus aureus reduce peptidoglycan chain length and cause aberrant cell division.

5. A practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols.

6. Tuning the moenomycin pharmacophore to enable discovery of bacterial cell wall synthesis inhibitors.

7. Complete characterization of the seventeen step moenomycin biosynthetic pathway.

8. Analysis of glycan polymers produced by peptidoglycan glycosyltransferases.

9. Isolated peptidoglycan glycosyltransferases from different organisms produce different glycan chain lengths.

Review 10. Bioactive oligosaccharide natural products.