Glykenin IVC

Glykenin IVC

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Category Antibiotics
Catalog number BBF-01270
CAS
Molecular Weight 971.13
Molecular Formula C46H82O21

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Description

It is produced by the strain of Basidiomycetes sp. It is a glycoside antibiotic, and has anti-gram-positive bacterial activity.

Specification

Synonyms (2S,17S,18S,22R)-2,17,18-Trihydroxy-22-[[2-O-[2-O-(6-O-acetyl-β-D-glucopyranosyl)-β-D-xylopyranosyl]-4-O-acetyl-β-D-xylopyranosyl]oxy]hexacosanoic acid
IUPAC Name (2S,17S,18S,22R)-22-[(2S,3R,4S,5R)-5-acetyloxy-3-[(2S,3R,4S,5R)-3-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-4-hydroxyoxan-2-yl]oxy-2,17,18-trihydroxyhexacosanoic acid
Canonical SMILES CCCCC(CCCC(C(CCCCCCCCCCCCCCC(C(=O)O)O)O)O)OC1C(C(C(CO1)OC(=O)C)O)OC2C(C(C(CO2)O)O)OC3C(C(C(C(O3)COC(=O)C)O)O)O
InChI InChI=1S/C46H82O21/c1-4-5-19-29(20-18-23-31(50)30(49)21-16-14-12-10-8-6-7-9-11-13-15-17-22-32(51)43(58)59)64-45-42(38(55)35(26-62-45)63-28(3)48)67-46-41(36(53)33(52)24-61-46)66-44-40(57)39(56)37(54)34(65-44)25-60-27(2)47/h29-42,44-46,49-57H,4-26H2,1-3H3,(H,58,59)/t29-,30+,31+,32+,33-,34-,35-,36+,37-,38+,39+,40-,41-,42-,44+,45+,46+/m1/s1
InChI Key NIVGVRFYLAQDRA-VWTJRZNYSA-N

Properties

Appearance Amorphous Powder
Antibiotic Activity Spectrum Gram-positive bacteria

Reference Reading

1. Structure elucidation of glykenin glycosidic antibiotics from Basidiomycetes sp. V. High-performance liquid chromatographic separation of components of glykenin
F Nishida, M Nishimura, K Harada, M Suzuki, V Meevootisom, T W Flegel, Y Thebtaranonth, S Intararuangsorn J Chromatogr A. 1994 Apr 1;664(2):195-202. doi: 10.1016/0021-9673(94)87008-x.
The glycosidic antibiotics of the glykenin (GK) family produced by Basidiomycetes sp. were separated into nine components (GK-I-VII and DG) by normal-phase chromatography. It was found that these components differ in the number and location of the acetyl groups in the sugar moiety. Each component (GK-I-VII and DG) was further separated into three isomers (A, B and C), which possess different aglycones, by reversed-phase chromatography on an ODS column with methanol-acetonitrile as eluent. The best composition of the eluent was found to be methanol-acetonitrile-1% trifluoroacetic acid (4:3.5:2.5). The profile analysis of GK-III-VII and DG was also carried out using a modified mobile phase. The combination of normal- and reversed-phase chromatography separated all components of the GK mixture except GK-I and II. The relationship between structure and separation behaviour of GK is discussed.

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