Tripropeptins, Novel Antimicrobial Agents Produced by Lysobacter sp. II. Structure Elucidation.

Hashizume, Hidetoshi; Hirosawa, Sehei; Sawa, Ryûichi; Muraoka, Yasuhiko; Ikeda, Daishiro; Naganawa, Hiroshi; Igarashi, Masayuki

doi:10.7164/antibiotics.57.52

Cited by 56 publications

(42 citation statements)

References 13 publications

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“…TPPs are cyclic depsipeptides consisting of eight amino acids and an isobranched chain fatty acid [14]. TPPs show potent antibacterial activities against Gram-positive bacteria including MRSA and VRE.…”

Section: Introductionmentioning

confidence: 99%

A New Type of Tripropeptin with Anteiso-branched Chain Fatty Acid from Lysobacter sp. BMK333-48F3

et al. 2008

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Branched chain amino acids are often utilized as the precursors of many lipid-containing bacterial secondary metabolites. The effect of isoleucine on the composition of the mixture of cyclic lipopeptide antibiotics, tripropeptins from Lysobacter sp. BMK333-48F3 was evaluated. As expected, a novel tripropeptin analog with an anteiso-branched fatty acid was produced.The new compound, TPPaiC shows potent antibacterial activity against Gram-positive bacteria including MRSA and VRE. On the other hand, no increase was observed in the production of other tripropeptins by the addition of isoleucine.

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Section: Introductionmentioning

confidence: 99%

A New Type of Tripropeptin with Anteiso-branched Chain Fatty Acid from Lysobacter sp. BMK333-48F3

et al. 2008

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“…11 NMR spectra and TLC of 9 and 11 were identical with those of 5. The enantiomeric excess of its methyl ester was determined by 1 H-NMR in the presence of (+)Eu(tfc) 3 .…”

Section: -Hydroxy-14-methylpentadecanoic Acid (5) (Scheme 1)mentioning

confidence: 99%

“…These results suggest that 3(S)-isomer 11 can be incorporated into TPPs only after enzymatic isomerization, which are easily understandable because natural TPPD has 3(R)-hydroxy-14-methylpentadecanoic acid. 3 The fatty acids were synthesized as outlined in Schemes 1 and 2. …”

Section: Introductionmentioning

confidence: 99%

Production of tripropeptins in media supplemented with precursors based on the biosynthetic pathway

Hashizume¹,

Nosaka²,

Hirosawa³

et al. 2006

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Tripropeptins (TPPs), the non-ribosomal cyclic depsipeptide antibiotics, are isolated from the culture broth of Lysobacter sp., and exhibit potent antimicrobial activity against gram-positive bacteria. TPPs consist of a common peptide ring composed of eight amino acids and a branched chain fatty acid from C-12 to C-17. Based on the biosynthetic pathway of branched chain fatty acids, the effects of supplement of their postulated biosynthetic precursors on production ratio of TPPs were examined. As expected, the corresponding TPP-components were predominantly produced by addition of leucine, isovaleric acid, 3-methyl-2-oxo-butanoic acid, 4-methyl-2-oxopentanoic acid and 3-hydroxy-14-methylpentadecanoic acids, but not by addition of valine.

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“…TPPC consists of a cyclic octapeptide core and a fatty acyl side chain, 13-methyl-3-hydroxy-tetradecanoic acid ( Fig. 1) (4,6). TPPC has a characteristic structure in that five of the eight amino acid residues in the peptide core are unusual amino acids: D-allo-threonine, L-trans-3-hydroxy proline, threo-beta-hydroxy-L-aspartic acid, threo-beta-hydroxy-D-aspartic acid, and D-proline.…”

mentioning

confidence: 99%

Tripropeptin C Blocks the Lipid Cycle of Cell Wall Biosynthesis by Complex Formation with Undecaprenyl Pyrophosphate

Hashizume

Sawa

Harada

et al. 2011

Antimicrob Agents Chemother

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Tripropeptins, Novel Antimicrobial Agents Produced by Lysobacter sp. II. Structure Elucidation.

Cited by 56 publications

References 13 publications

A New Type of Tripropeptin with Anteiso-branched Chain Fatty Acid from Lysobacter sp. BMK333-48F3

A New Type of Tripropeptin with Anteiso-branched Chain Fatty Acid from Lysobacter sp. BMK333-48F3

Production of tripropeptins in media supplemented with precursors based on the biosynthetic pathway

Tripropeptin C Blocks the Lipid Cycle of Cell Wall Biosynthesis by Complex Formation with Undecaprenyl Pyrophosphate

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