Thioxamycin

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Thioxamycin
Category Antibiotics
Catalog number BBF-02692
CAS 124883-37-0
Molecular Weight 1265.29
Molecular Formula C52H48N16O15S4
Purity ≥98%

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Description

Thioxamycin is produced by the strain of Str. sp. DP94. The minimum inducing concentration of X to the promoter TIP-1 was 80 ng/mL.

Specification

Synonyms Sulfomycin I, 58-(1-carboxyethenyl)-28-deethylidene-14-de(2-hydroxypropylidene)-21-demethoxy-17,31-didemethyl-28-methyl-14-((methylthio)methyl)-30-thia-
Storage Store at RT
IUPAC Name 2-[2-[2-[2-[[(14S,17R)-14-[(1R)-1-hydroxyethyl]-31-methyl-38,41-dimethylidene-17-(methylsulfanylmethyl)-12,15,22,29,36,39-hexaoxo-19,43-dioxa-9,26,33-trithia-3,13,16,23,30,37,40,45,46,47,48,49-dodecazaheptacyclo[40.2.1.18,11.118,21.125,28.132,35.02,7]nonatetraconta-1(44),2(7),3,5,8(49),10,18(48),20,25(47),27,32(46),34,42(45)-tridecaene-4-carbonyl]amino]prop-2-enoylamino]prop-2-enoylamino]prop-2-enoylamino]prop-2-enoic acid
Canonical SMILES CC1C2=NC(=CS2)C(=O)NC(=C)C(=O)NC(=C)C3=NC(=CO3)C4=C(C=CC(=N4)C(=O)NC(=C)C(=O)NC(=C)C(=O)NC(=C)C(=O)NC(=C)C(=O)O)C5=NC(=CS5)C(=O)NC(C(=O)NC(C6=NC(=CO6)C(=O)NCC7=NC(=CS7)C(=O)N1)CSC)C(C)O
InChI InChI=1S/C52H48N16O15S4/c1-19(38(70)55-20(2)41(73)60-25(7)52(80)81)54-39(71)21(3)56-43(75)28-11-10-27-37(62-28)29-13-82-48(64-29)23(5)58-40(72)22(4)57-45(77)32-17-86-50(66-32)24(6)59-44(76)31-16-85-35(61-31)12-53-42(74)30-14-83-49(65-30)34(15-84-9)63-47(79)36(26(8)69)68-46(78)33-18-87-51(27)67-33/h10-11,13-14,16-18,24,26,34,36,69H,1-5,7,12,15H2,6,8-9H3,(H,53,74)(H,54,71)(H,55,70)(H,56,75)(H,57,77)(H,58,72)(H,59,76)(H,60,73)(H,63,79)(H,68,78)(H,80,81)/t24?,26-,34+,36+/m1/s1
InChI Key GATPMIKWKVOBMF-GZASFEHQSA-N

Properties

Appearance White Powder
Melting Point 240-245°C

Reference Reading

1. Isolation and characterization of thioxamycin
M Matsumoto, Y Kawamura, Y Yasuda, T Tanimoto, K Matsumoto, T Yoshida, J Shoji J Antibiot (Tokyo). 1989 Oct;42(10):1465-9. doi: 10.7164/antibiotics.42.1465.
A new peptide antibiotic named thioxamycin which contained thiazole and oxazole rings was isolated from the culture broth of Streptomyces sp. The antibiotic is acidic and lipophilic in nature. A molecular formula, C52H48N16O15S4, was indicated by elemental analysis and MS. One mol of threonine and three unusual amino acids were detected by amino acid analysis of the acid hydrolysate. The antibiotic is active in vitro against anaerobic Gram-positive and Gram-negative bacteria and also aerobic Gram-positive bacteria.

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