Literature DB >> 30108957

Crystallomycin revisited after 60 years: aspartocins B and C.

Anton P Tyurin1,2, Vera A Alferova1, Alexander S Paramonov2, Maxim V Shuvalov1,3, Irina A Malanicheva1, Natalia E Grammatikova1, Pavel N Solyev4, Shaowei Liu5, Chenghang Sun5, Igor A Prokhorenko1,2, Tatyana A Efimenko1, Larisa P Terekhova1, Olga V Efremenkova1, Zakhar O Shenkarev2,6, Vladimir A Korshun1,2.   

Abstract

The study of an archived sample of crystallomycin complex using HPLC, ESI HRMS, and 2D NMR showed that two major components of the antibiotic, compounds 1 and 2, are lipopeptides having the same peptide core, Asp1-cyclo(Dab2-Pip3-MeAsp4-Asp5-Gly6-Asp7-Gly8-Dab9-Val10-Pro11-), N-acylated either with Δ3-iso-tetradecenoyl or Δ3-anteiso-pentadecenoyl that are identical to aspartocins C and B, respectively. According to the 2D NMR study, compound 2 in DMSO solution exists as a mixture of four conformers. The producing strain was identified as Streptomyces griseorubens. Compounds 1 and 2 have considerable Ca2+-dependent activity against Gram-positive bacteria including five MRSA strains.

Entities:  

Year:  2018        PMID： 30108957      PMCID： PMC6071864          DOI： 10.1039/c8md00002f

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  21 in total

1.  [Chemical composition of crystallomycin].

Authors:  N N LOMAKINA; M G BRAZHNIKOVA
Journal:  Biokhimiia       Date:  1959 May-Jun

2.  Zaomycin, a new antibiotic from a Streptomyces sp.

Authors:  Y HINUMA
Journal:  J Antibiot (Tokyo)       Date:  1954-08       Impact factor: 2.649

3.  Novel antimicrobial lipopeptides with long in vivo half-lives.

Authors:  Chris J Pasetka; Douglas J Erfle; Dale R Cameron; Jacob J Clement; Evelina Rubinchik
Journal:  Int J Antimicrob Agents       Date:  2009-12-16       Impact factor: 5.283

4.  Structure of the lipopeptide antibiotic tsushimycin.

Authors:  Gábor Bunkóczi; László Vértesy; George M Sheldrick
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2005-07-20

5.  Studies on tsushimycin. II. The structures of constituent fatty acids.

Authors:  J Shoji; H Otsuka
Journal:  J Antibiot (Tokyo)       Date:  1969-10       Impact factor: 2.649

6.  In vivo pharmacodynamics of new lipopeptide MX-2401.

Authors:  W A Craig; D R Andes; T Stamstad
Journal:  Antimicrob Agents Chemother       Date:  2010-09-20       Impact factor: 5.191

7.  Friulimicins: novel lipopeptide antibiotics with peptidoglycan synthesis inhibiting activity from Actinoplanes friuliensis sp. nov. I. Taxonomic studies of the producing microorganism and fermentation.

Authors:  W Aretz; J Meiwes; G Seibert; G Vobis; J Wink
Journal:  J Antibiot (Tokyo)       Date:  2000-08       Impact factor: 2.649

Review 8.  Natural products to drugs: daptomycin and related lipopeptide antibiotics.

Authors:  Richard H Baltz; Vivian Miao; Stephen K Wrigley
Journal:  Nat Prod Rep       Date:  2005-11-04       Impact factor: 13.423

9.  NMR structure determination and calcium binding effects of lipopeptide antibiotic daptomycin.

Authors:  Lee-Jon Ball; Catherine M Goult; James A Donarski; Jason Micklefield; Vasudevan Ramesh
Journal:  Org Biomol Chem       Date:  2004-06-15       Impact factor: 3.876

10.  Solid-state NMR characterization of amphomycin effects on peptidoglycan and wall teichoic acid biosyntheses in Staphylococcus aureus.

Authors:  Manmilan Singh; James Chang; Lauryn Coffman; Sung Joon Kim
Journal:  Sci Rep       Date:  2016-08-19       Impact factor: 4.379
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  1 in total

Review 1.  The calcium-dependent lipopeptide antibiotics: structure, mechanism, & medicinal chemistry.

Authors:  Thomas M Wood; Nathaniel I Martin
Journal:  Medchemcomm       Date:  2019-03-21       Impact factor: 3.597
  1 in total

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