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Vicenistatin M

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Category Others
Catalog number BBF-02960
CAS 312532-50-6
Molecular Weight 501.70
Molecular Formula C30H47NO5

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Streptomyces sp. HC-34. It is a homologue of Mycarose replacing amino sugars in the Vicenstatin molecule, and it loses the cytotoxicity of Vicenstatin.

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Synonyms (6S,7S,18S)-20-aza-6,10,12,18-tetramethyl-7-O-(2',6'-dideoxy-3'-C-methyl-β-D-ribo-hexopyranosyl)-cycloicosa-2,4,9,12,14-pentaen-1-one; (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-((2R,4S,5R,6R)-4,5-Dihydroxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one; Vicenistatine M
IUPAC Name (3E,5E,7S,8S,10E,13E,15E,19S)-8-[(2R,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-7,11,13,19-tetramethyl-1-azacycloicosa-3,5,10,13,15-pentaen-2-one
Canonical SMILES CC1CCC=CC=C(CC(=CCC(C(C=CC=CC(=O)NC1)C)OC2CC(C(C(O2)C)O)(C)O)C)C
InChI InChI=1S/C30H47NO5/c1-21-12-8-7-9-13-23(3)20-31-27(32)15-11-10-14-24(4)26(17-16-22(2)18-21)36-28-19-30(6,34)29(33)25(5)35-28/h7-8,10-12,14-16,23-26,28-29,33-34H,9,13,17-20H2,1-6H3,(H,31,32)/b8-7+,14-10+,15-11+,21-12+,22-16+/t23-,24-,25+,26-,28-,29+,30-/m0/s1
InChI Key YVXZXDRTHFRUIX-LPLNQVICSA-N
Appearance White Powder
Boiling Point 672.7±55.0°C at 760 mmHg
Melting Point 201-210°C
Density 1.1±0.1 g/cm3
Solubility Soluble in Methanol
1. Isolation and structure elucidation of vicenistatin M, and importance of the vicenisamine aminosugar for exerting cytotoxicity of vicenistatin
Y Matsushima, T Nakayama, M Fujita, R Bhandari, T Eguchi, K Shindo, K Kakinuma J Antibiot (Tokyo). 2001 Mar;54(3):211-9. doi: 10.7164/antibiotics.54.211.
A new analogue of vicenistatin was isolated from the producing strain Streptomyces sp. HC-34. A characteristic of the elucidated structure involved the existence of a neutral sugar mycarose instead of an aminosugar vicenisamine of vicenistatin. The absolute stereochemistry of the new analogue (named as vicenistatin M) was determined by the synthesis of D-mycarose and of vicenistatin M itself. Biological testing of vicenistatin M suggested the importance of vicenisamine for exerting the cytotoxicity of vicenistatin.

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