Viscosin

• CAT Number: I038078
• CAS Number: 27127-62-4
• Molecular Formula: C54H95N9O16
• Molecular Weight: 1126.401
• Purity: 98%
• Synonyms: Viscosin
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (4R)-5-[[(3S,6R,9S,12R,15S,18R,21R,22R)-3-[(2S)-butan-2-yl]-6,12-bis(hydroxymethyl)-22-methyl-9,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-4-[[(2S)-2-[[(3R)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
• InChI: InChI=1S/C54H95N9O16/c1-13-15-16-17-18-19-34(66)25-41(67)55-36(22-28(3)4)47(71)56-35(20-21-42(68)69)46(70)63-45-33(12)79-54(78)44(32(11)14-2)62-51(75)40(27-65)60-48(72)37(23-29(5)6)57-50(74)39(26-64)59-49(73)38(24-30(7)8)58-52(76)43(31(9)10)61-53(45)77/h28-40,43-45,64-66H,13-27H2,1-12H3,(H,55,67)(H,56,71)(H,57,74)(H,58,76)(H,59,73)(H,60,72)(H,61,77)(H,62,75)(H,63,70)(H,68,69)/t32-,33+,34+,35+,36-,37-,38-,39+,40+,43+,44-,45+/m0/s1
• InChIKey: QYEWAEAWMXRMHB-YFTUCIGFSA-N
• SMILES: O=C(O)CC[C@@H](NC([C@@H](NC(C[C@H](O)CCCCCCC)=O)CC(C)C)=O)C(N[C@H]1C(N[C@H](C(C)C)C(N[C@@H](CC(C)C)C(N[C@H](CO)C(N[C@@H](CC(C)C)C(N[C@H](CO)C(N[C@@H]([C@H](CC)C)C(O[C@@H]1C)=O)=O)=O)=O)=O)=O)=O)=O

Viscose (Cat. No: I038078) is a peptide lipid biosurfactant and plant pathogen, and also a cyclic lipopeptide. The structural types, mechanism of action, and extensive biological activities of cyclic lipopeptides have made them a hot spot for new drug screening.

Reference

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2: Geudens N, Nasir MN, Crowet JM, Raaijmakers JM, Fehér K, Coenye T, Martins JC, Lins L, Sinnaeve D, Deleu M. Membrane Interactions of Natural Cyclic Lipodepsipeptides of the Viscosin Group. Biochim Biophys Acta Biomembr. 2017 Mar;1859(3):331-339. doi: 10.1016/j.bbamem.2016.12.013. Epub 2016 Dec 20. PubMed PMID: 28007479.
3: Kissoyan KAB, Drechsler M, Stange EL, Zimmermann J, Kaleta C, Bode HB, Dierking K. Natural C. elegans Microbiota Protects against Infection via Production of a Cyclic Lipopeptide of the Viscosin Group. Curr Biol. 2019 Mar 18;29(6):1030-1037.e5. doi: 10.1016/j.cub.2019.01.050. Epub 2019 Feb 28. PubMed PMID: 30827913.
4: Bak F, Bonnichsen L, Jørgensen NO, Nicolaisen MH, Nybroe O. The biosurfactant viscosin transiently stimulates n-hexadecane mineralization by a bacterial consortium. Appl Microbiol Biotechnol. 2015 Feb;99(3):1475-83. doi: 10.1007/s00253-014-6054-3. Epub 2014 Sep 14. PubMed PMID: 25216581; PubMed Central PMCID: PMC4306737.
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12: Burke TR Jr, Chandrasekhar B. Preparative reversed-phase high-performance liquid chromatography in the synthesis of viscosin, a cyclic depsipeptide. J Chromatogr. 1989 Dec 22;484:293-8. PubMed PMID: 2613788.
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19: Hiramoto M, Okada K, Nagai S, Kawamoto H. The structure of viscosin, a peptide antibiotic. I. Syntheses of D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin. Chem Pharm Bull (Tokyo). 1971 Jul;19(7):1308-14. PubMed PMID: 4998540.
20: Hiramoto M, Okada K, Nagai S. The structure of viscosin, a peptide antibiotic. II. Syntheses of D- and L-3-hydroxyacylhexapeptides including the proposed structure of viscosin and its optical isomers. Chem Pharm Bull (Tokyo). 1971 Jul;19(7):1315-20. PubMed PMID: 4935900.