Diolmycin B2

Diolmycin B2

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Category Antibiotics
Catalog number BBF-01158
CAS
Molecular Weight 274.31
Molecular Formula C16H18O4

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Description

It is produced by the strain of Streptomyces sp. WK-2955. It is an antibiotic with anticoccidial activity.

Specification

Related CAS 150346-22-8 (R-isomer)
IUPAC Name (2S,3S)-1,4-bis(4-hydroxyphenyl)butane-2,3-diol
Canonical SMILES C1=CC(=CC=C1CC(C(CC2=CC=C(C=C2)O)O)O)O
InChI InChI=1S/C16H18O4/c17-13-5-1-11(2-6-13)9-15(19)16(20)10-12-3-7-14(18)8-4-12/h1-8,15-20H,9-10H2/t15-,16-/m0/s1
InChI Key HSXZRJJGRJUHLX-HOTGVXAUSA-N

Properties

Antibiotic Activity Spectrum Parasites
Boiling Point 544.1 °C at 760 mmHg
Density 1.315 g/cm3

Reference Reading

1. Diolmycins, new anticoccidial agents produced by Streptomyces sp. I. Production, isolation and physico-chemical and biological properties
N Tabata, H Tomoda, Y Takahashi, K Haneda, Y Iwai, H B Woodruff, S Omura J Antibiot (Tokyo). 1993 May;46(5):756-61. doi: 10.7164/antibiotics.46.756.
Streptomyces sp. WK-2955, a soil isolate, was found to produce a series of new anticoccidial compounds. Four active compounds, designated diolmycins A1, A2, B1 and B2, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography, gel filtration on Sephadex LH-20, and preparative HPLC. Diolmycins inhibited the growth of Eimeria tenella in an in vitro assay system using BHK-21 cells as a host. No schizont in the cells was observed at concentrations of 0.02-2.0 micrograms/ml for diolmycin A1, at 0.2-2.0 micrograms/ml for diolmycin A2, and at 20 micrograms/ml for diolmycins B1 and B2.
2. Diolmycins, new anticoccidial agents produced by Streptomyces sp. II. Structure elucidation of diolmycins A1, A2, B1 and B2, and synthesis of diolmycin A1
N Tabata, T Sunazuka, H Tomoda, T Nagamitsu, Y Iwai, S Omura J Antibiot (Tokyo). 1993 May;46(5):762-9. doi: 10.7164/antibiotics.46.762.
The structures of diolmycins A1, A2, B1 and B2, novel anticoccidial agents, were determined by spectroscopic analyses. Diolmycins A1 and A2 are stereoisomers with the structure of 1-(3-indolyl)-4-(p-hydroxyphenyl)-2,3-butanediol. From the chemical synthesis of the erythro-isomer, the relative configurations of diolmycins A1 and A2 were determined to be the erythro- and threo-isomers, respectively. The stereoisomers, diolmycins B1 and B2, were also deduced to be erythro- and threo-1,4-di-(p-hydroxyphenyl)-2,3-butanediol, respectively.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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