Lipohexin

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Category Antibiotics
Catalog number BBF-02263
CAS
Molecular Weight 764.99
Molecular Formula C39H68N6O9

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Description

It is produced by the strain of Moeszia lindtneri HKI-0054 Paecilomyces sp. HKI-0055 and HKI-0096. It's a peptide antibiotic. It has anti-gram-positive bacterial effect. It had competitive inhibitory effect on human placental proline endopeptidase with IC50 of 3.5 μmol/L. It inhibits the proline endopeptidase from the Flavobacterium meningoseptiu with IC50 of 25 μmol/L.

Specification

IUPAC Name 3-[[2-methyl-2-[[2-methyl-2-[[2-methyl-2-[[2-methyl-2-[[(2S)-1-(2-methyl-3-oxotetradecanoyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoic acid
Canonical SMILES CCCCCCCCCCCC(=O)C(C)C(=O)N1CCCC1C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NCCC(=O)O
InChI InChI=1S/C39H68N6O9/c1-11-12-13-14-15-16-17-18-19-22-28(46)26(2)31(50)45-25-20-21-27(45)30(49)41-37(5,6)33(52)43-39(9,10)35(54)44-38(7,8)34(53)42-36(3,4)32(51)40-24-23-29(47)48/h26-27H,11-25H2,1-10H3,(H,40,51)(H,41,49)(H,42,53)(H,43,52)(H,44,54)(H,47,48)/t26?,27-/m0/s1
InChI Key PMRLBLJJGVOETQ-GEVKEYJPSA-N

Properties

Appearance White Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 191°C (dec.)

Reference Reading

1. Lipohexin, a new inhibitor of prolyl endopeptidase from Moeszia lindtneri (HKI-0054) and Paecilomyces sp. (HKI-0055; HKI-0096). II. Inhibitory activities and specificity
C Christner, M Zerlin, U Gräfe, S Heinze, G Küllertz, G Fischer J Antibiot (Tokyo). 1997 May;50(5):384-9. doi: 10.7164/antibiotics.50.384.
The new proline-containing lipohexapeptide lipohexin (I) isolated from three fungal strains, Moeszia lindtneri (HKI-0054) and Paecilomyces sp. (HKI-0055 and HKI-0096) is a competitive inhibitor of prolyl endopeptidase (PEP) from human placenta with IC50 of 3.5 microM. Specificity of lipohexin (I) is indicated by the much weaker inhibitory activity against bacterial prolyl endopeptidase from Flavobacterium meningosepticum (IC50 25 microM). No effect of lipohexin (I) was found on the activity of mechanistically related proteases such as proline specific proteases and other serine proteases.
2. Lipohexin, a new inhibitor of prolyl endopeptidase from Moeszia lindtneri (HKI-0054) and Paecilomyces sp. (HKI-0055; HKI-0096). I. Screening, isolation and structure elucidation
S Heinze, M Ritzau, W Ihn, H Hülsmann, B Schlegel, K Dornberger, W F Fleck, M Zerlin, C Christner, U Gräfe, G Küllertz, G Fischer J Antibiot (Tokyo). 1997 May;50(5):379-83. doi: 10.7164/antibiotics.50.379.
Lipohexin was isolated as a novel lipohexapeptide (I) (C39H68N6O9) from three fungal strains, Moeszia lindtneri HKI-0054, Paecilomyces sp. HKI-0055 and Paecilomyces sp. HKI-0096. The structure was elucidated by detailed mass spectrometric and NMR experiments. The proline-containing peptide displays moderate antibacterial activity against Bacillus subtilis ATCC 6633 and inhibits competitively the prolyl endopeptidase from human placenta.

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