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Butalactin

Name: Butalactin
Brand: BOC Sciences
Rating: 5 (1 reviews)

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category	Antibiotics
Catalog number	BBF-00190
CAS	132605-69-7
Molecular Weight	242.22
Molecular Formula	C11H14O6

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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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

Butalactin is a new butanolide antibiotic produced by Streptomyces sp. HIL Y-8636923. It has weak anti-Gram-positive and negative bacteria activity.

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IUPAC Name	(3R,4S)-3-hydroxy-4-(hydroxymethyl)-3-[(E)-3-(3-methyloxiran-2-yl)prop-2-enoyl]oxolan-2-one
Canonical SMILES	CC1C(O1)C=CC(=O)C2(C(COC2=O)CO)O
InChI	InChI=1S/C11H14O6/c1-6-8(17-6)2-3-9(13)11(15)7(4-12)5-16-10(11)14/h2-3,6-8,12,15H,4-5H2,1H3/b3-2+/t6?,7-,8?,11+/m0/s1
InChI Key	NDWZCKPIOWDQOR-YIVRGOCWSA-N

Appearance	Oil
Antibiotic Activity Spectrum	Gram-positive bacteria; Gram-negative bacteria
Boiling Point	485°C at 760 mmHg
Density	1.373 g/cm3
Solubility	Soluble in Water, methanol, acetonitrile, chloroform

1. Butalactin, a new butanolide antibiotic. Taxonomy, fermentation, isolation and biological activity

C M Franco, U P Borde, E K Vijayakumar, S Chatterjee, J Blumbach, B N Ganguli J Antibiot (Tokyo). 1991 Feb;44(2):225-31. doi: 10.7164/antibiotics.44.225.

Butalactin, [2-(4',5'-epoxy-hex-2'(E)-en)oyl-2-hydroxy-3-hydroxymethyl-2, 3-(Z)-butanolide] is a new antibiotic produced by Streptomyces sp. HIL Y-86,36923. Taxonomically, the producing organism most closely resembles Streptomyces corchorusii. The strain also produces cineromycin B. Though butalactin is structurally related to 'signal molecules' such as A-factor, the anthracycline inducing factors and the virginiae butanolides, it does not show inducing activity for antibiotic production or aerial mycelium formation in the indicator strain. Butalactin possesses a weak antibiotic activity against Gram-positive and Gram-negative bacteria.

2. Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species

Toshihiko Ueki, Takamasa Kinoshita Org Biomol Chem. 2004 Oct 7;2(19):2777-85. doi: 10.1039/B407820A. Epub 2004 Aug 23.

Butalactin (1a) and lactone II (2a) have been synthesized starting from (S)-malic acid and sorbic acid by a straightforward route. The absolute stereochemistry of 1a and 2a was unambiguously established by this synthesis.

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