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Literature DB >> 19783144

Functional and biochemical analysis of a key series of ramoplanin analogues.

Xiao Fang¹, Joonwoo Nam, Dongwoo Shin, Yosup Rew, Dale L Boger, Suzanne Walker.

Abstract

Ramoplanin is a potent lipoglycodepsipeptide antibiotic that is active against a wide range of Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococcus (VRE). It acts as an inhibitor of peptidoglycan (PG) biosynthesis that disrupts glycan chain polymerization by binding and sequestering Lipid II, a PG precursor. Herein, we report the functional antimicrobial activity (MIC, S. aureus) and fundamental biochemical assessments against a peptidoglycan glycosyltransferase (Escherichia coli PBP1b) of a set of key alanine scan analogues of ramoplanin that provide insight into the importance and role of each of its individual amino acid residues.

Entities: Chemical Disease Species

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Year: 2009 PMID： 19783144 PMCID： PMC2767165 DOI： 10.1016/j.bmcl.2009.09.001

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

14 in total

1. A new structure for the substrate-binding antibiotic ramoplanin.

Authors: M C Lo; J S Helm; G Sarngadharan; I Pelczer; S Walker
Journal: J Am Chem Soc Date: 2001-09-05 Impact factor: 15.419

2. Complexation of peptidoglycan intermediates by the lipoglycodepsipeptide antibiotic ramoplanin: minimal structural requirements for intermolecular complexation and fibril formation.

Authors: Predrag Cudic; James K Kranz; Douglas C Behenna; Ryan G Kruger; Hellina Tadesse; A Joshua Wand; Yuri I Veklich; John W Weisel; Dewey G McCafferty
Journal: Proc Natl Acad Sci U S A Date: 2002-05-28 Impact factor: 11.205

3. Total synthesis of the ramoplanin A2 and ramoplanose aglycon.

Authors: Wanlong Jiang; Jutta Wanner; Richard J Lee; Pierre-Yves Bounaud; Dale L Boger
Journal: J Am Chem Soc Date: 2002-05-15 Impact factor: 15.419

4. Total synthesis of the ramoplanin A2 and ramoplanose aglycon.

Authors: Wanlong Jiang; Jutta Wanner; Richard J Lee; Pierre-Yves Bounaud; Dale L Boger
Journal: J Am Chem Soc Date: 2003-02-19 Impact factor: 15.419

5. Ramoplanin inhibits bacterial transglycosylases by binding as a dimer to lipid II.

Authors: Yanan Hu; Jeremiah S Helm; Lan Chen; Xiang-Yang Ye; Suzanne Walker
Journal: J Am Chem Soc Date: 2003-07-23 Impact factor: 15.419

6. 3D structure of ramoplanin: a potent inhibitor of bacterial cell wall synthesis.

Authors: M Kurz; W Guba
Journal: Biochemistry Date: 1996-09-24 Impact factor: 3.162

7. Dissecting ramoplanin: mechanistic analysis of synthetic ramoplanin analogues as a guide to the design of improved antibiotics.

Authors: Lan Chen; Yanqiu Yuan; Jeremiah S Helm; Yanan Hu; Yosup Rew; Dongwoo Shin; Dale L Boger; Suzanne Walker
Journal: J Am Chem Soc Date: 2004-06-23 Impact factor: 15.419

8. Rethinking ramoplanin: the role of substrate binding in inhibition of peptidoglycan biosynthesis.

Authors: Jeremiah S Helm; Lan Chen; Suzanne Walker
Journal: J Am Chem Soc Date: 2002-11-27 Impact factor: 15.419

9. Total synthesis and structure of the ramoplanin A1 and A3 aglycons: two minor components of the ramoplanin complex.

Authors: Dongwoo Shin; Yosup Rew; Dale L Boger
Journal: Proc Natl Acad Sci U S A Date: 2004-06-02 Impact factor: 11.205

10. Total synthesis and examination of three key analogues of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity.

Authors: Yosup Rew; Dongwoo Shin; Inkyu Hwang; Dale L Boger
Journal: J Am Chem Soc Date: 2004-02-04 Impact factor: 15.419

5 in total

Functional and biochemical analysis of a key series of ramoplanin analogues.

1. A new structure for the substrate-binding antibiotic ramoplanin.

2. Complexation of peptidoglycan intermediates by the lipoglycodepsipeptide antibiotic ramoplanin: minimal structural requirements for intermolecular complexation and fibril formation.

3. Total synthesis of the ramoplanin A2 and ramoplanose aglycon.

4. Total synthesis of the ramoplanin A2 and ramoplanose aglycon.

5. Ramoplanin inhibits bacterial transglycosylases by binding as a dimer to lipid II.

6. 3D structure of ramoplanin: a potent inhibitor of bacterial cell wall synthesis.

7. Dissecting ramoplanin: mechanistic analysis of synthetic ramoplanin analogues as a guide to the design of improved antibiotics.

8. Rethinking ramoplanin: the role of substrate binding in inhibition of peptidoglycan biosynthesis.

9. Total synthesis and structure of the ramoplanin A1 and A3 aglycons: two minor components of the ramoplanin complex.

10. Total synthesis and examination of three key analogues of ramoplanin: a lipoglycodepsipeptide with potent antibiotic activity.

1. Host-guest chemistry of the peptidoglycan.

2. Pharmacological properties of NAI-603, a well-tolerated semisynthetic derivative of ramoplanin.

3. The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.

4. Production of the Ramoplanin Activity Analogue by Double Gene Inactivation.

Review 5. Emerging peptide antibiotics with therapeutic potential.