Watasemycin A

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Category Antibiotics
Catalog number BBF-02974
CAS
Molecular Weight 352.47
Molecular Formula C16H20N2O3S2

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Description

It is produced by the strain of Streptomyces sp. TP-A0597. It has anti-staphylococcus aureus, bacillus subtilis, proteus bizarre and cryptococcus neoformans activity with MIC (μg/mL) of 12.5, 25.0, 0.39 and 20.0, respectively.

Specification

Synonyms 4-Thiazolidinecarboxylic acid, 2-[(4R,5S)-4,5-dihydro-2-(2-hydroxyphenyl)-5-methyl-4-thiazolyl]-3,4-dimethyl-, (2S,4S)-
IUPAC Name (2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid
Canonical SMILES CC1C(N=C(S1)C2=CC=CC=C2O)C3N(C(CS3)(C)C(=O)O)C
InChI InChI=1S/C16H20N2O3S2/c1-9-12(14-18(3)16(2,8-22-14)15(20)21)17-13(23-9)10-6-4-5-7-11(10)19/h4-7,9,12,14,19H,8H2,1-3H3,(H,20,21)/t9-,12+,14-,16+/m0/s1
InChI Key NOEXPDVJQLSPPC-UODBANLJSA-N

Properties

Appearance Light Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Yeast
Boiling Point 548.6±60.0°C at 760 mmHg
Melting Point 62-65°C
Density 1.4±0.1 g/cm3
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Watasemycins A and B, new antibiotics produced by Streptomyces sp. TP-A0597
Omomitsu Sasaki, Yasuhiro Igarashi, Noriko Saito, Tamotsu Furumai J Antibiot (Tokyo). 2002 Mar;55(3):249-55. doi: 10.7164/antibiotics.55.249.
Two novel antibiotics, watasemycins A and B, were isolated from the fermentation broth of an actinomycete strain. The producing strain TP-A0597 was isolated from the seawater sample collected in Toyama Bay, Japan and identified as Streptomyces sp. based on the taxonomic study. The new antibiotics were obtained by solvent extraction and chromatographic purification and spectroscopic analyses identified that they were new analogs of thiazostatins. Watasemycin possesses a methyl group at 5'-position of thiazostatin instead of a hydrogen atom. Watasemycins showed antibiotic activity against Gram-positive and negative bacteria and yeast.

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