Althiomycin
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MedKoo CAT#: 592716

CAS#: 12656-40-5

Description: Althiomycin, also known as matamycin, is a thiazole antibiotic, effective against Gram-positive and Gram-negative bacteria. Isolated from Streptomyces matensis, Althiomycin was first described by Margalith et al. in 1959. It acts a protein synthesis inhibitor and its site of action is the 50S subunit of the bacterial ribosome.


Chemical Structure

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Althiomycin
CAS# 12656-40-5

Theoretical Analysis

MedKoo Cat#: 592716
Name: Althiomycin
CAS#: 12656-40-5
Chemical Formula: C16H17N5O6S2
Exact Mass: 439.062
Molecular Weight: 439.46
Elemental Analysis: C, 43.73; H, 3.90; N, 15.94; O, 21.84; S, 14.59

Price and Availability

Size Price Availability Quantity
2.0mg USD 165.0 Same day
5.0mg USD 350.0 Same day
10.0mg USD 550.0 Same day
25.0mg USD 1250.0 Same day
50.0mg USD 2250.0 Same day
100.0mg USD 4050.0 Same day
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Synonym: Althiomycin, NSC 102809, NSC-102809; NSC102809; 116-A; Matamycin;

IUPAC/Chemical Name: N-((S)-2-hydroxy-1-((S)-4-(4-methoxy-2-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl)-4,5-dihydrothiazol-2-yl)ethyl)-2-((E)-(hydroxyimino)methyl)thiazole-4-carboxamide

InChi Key: VQQNQKXWJMRPHT-YNYXEJBLSA-N

InChi Code: InChI=1S/C16H17N5O6S2/c1-27-8-2-13(23)21(4-8)16(25)11-7-29-15(20-11)9(5-22)19-14(24)10-6-28-12(18-10)3-17-26/h2-3,6,9,11,22,26H,4-5,7H2,1H3,(H,19,24)/b17-3+/t9-,11+/m0/s1

SMILES Code: O=C(N[C@H](C1=N[C@H](CS1)C(N2C(C=C(C2)OC)=O)=O)CO)C3=CSC(/C=N/O)=N3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 439.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Pan X, Sun C, Tang M, You J, Osire T, Zhao Y, Xu M, Zhang X, Shao M, Yang S, Yang T, Rao Z. LysR-Type Transcriptional Regulator MetR Controls Prodigiosin Production, Methionine Biosynthesis, Cell Motility, H2O2 Tolerance, Heat Tolerance, and Exopolysaccharide Synthesis in Serratia marcescens. Appl Environ Microbiol. 2020 Feb 3;86(4):e02241-19. doi: 10.1128/AEM.02241-19. PMID: 31791952; PMCID: PMC6997736.

2: Pan X, Sun C, Tang M, Liu C, Zhang J, You J, Osire T, Sun Y, Zhao Y, Xu M, Yang T, Rao Z. Loss of Serine-Type D-Ala-D-Ala Carboxypeptidase DacA Enhances Prodigiosin Production in Serratia marcescens. Front Bioeng Biotechnol. 2019 Dec 3;7:367. doi: 10.3389/fbioe.2019.00367. PMID: 31850328; PMCID: PMC6901396.

3: Gerc AJ, Stanley-Wall NR, Coulthurst SJ. Role of the phosphopantetheinyltransferase enzyme, PswP, in the biosynthesis of antimicrobial secondary metabolites by Serratia marcescens Db10. Microbiology. 2014 Aug;160(Pt 8):1609-1617. doi: 10.1099/mic.0.078576-0. Epub 2014 May 20. PMID: 24847000; PMCID: PMC4117218.

4: Gerc AJ, Song L, Challis GL, Stanley-Wall NR, Coulthurst SJ. The insect pathogen Serratia marcescens Db10 uses a hybrid non-ribosomal peptide synthetase-polyketide synthase to produce the antibiotic althiomycin. PLoS One. 2012;7(9):e44673. doi: 10.1371/journal.pone.0044673. Epub 2012 Sep 18. PMID: 23028578; PMCID: PMC3445576.

5: Cortina NS, Revermann O, Krug D, Müller R. Identification and characterization of the althiomycin biosynthetic gene cluster in Myxococcus xanthus DK897. Chembiochem. 2011 Jun 14;12(9):1411-6. doi: 10.1002/cbic.201100154. Epub 2011 May 27. PMID: 21626639.

6: Gaspari F, Paitan Y, Mainini M, Losi D, Ron EZ, Marinelli F. Myxobacteria isolated in Israel as potential source of new anti-infectives. J Appl Microbiol. 2005;98(2):429-39. doi: 10.1111/j.1365-2672.2004.02477.x. PMID: 15659197.

7: Zarantonello P, Leslie CP, Ferritto R, Kazmierski WM. Total synthesis and semi-synthetic approaches to analogues of antibacterial natural product althiomycin. Bioorg Med Chem Lett. 2002 Feb 25;12(4):561-5. doi: 10.1016/s0960-894x(01)00802-2. PMID: 11844672.

8: Kunze B, Reichenbach H, Augustiniak H, Höfle G. Isolation and identification of althiomycin from Cystobacter fuscus (myxobacterales). J Antibiot (Tokyo). 1982 May;35(5):635-6. doi: 10.7164/antibiotics.35.635. PMID: 6809724.

9: Kirst HA, Szymanski EF, Dorman DE, Occolowitz JL, Jones ND, Chaney MO, Hamill RL, Hoehn MM. Structure of althiomycin. J Antibiot (Tokyo). 1975 Apr;28(4):286-91. doi: 10.7164/antibiotics.28.286. PMID: 1150528.

10: Sakakibara H, Naganawa H, Ono M, Maeda K, Umezawa H. The structure of althiomycin. J Antibiot (Tokyo). 1974 Nov;27(11):897-9. doi: 10.7164/antibiotics.27.897. PMID: 4452663.

11: Pestka S. Antibiotics as probes of ribosome structure: binding of chloramphenicol and erythromycin to polyribosomes; effect of other antibiotics. Antimicrob Agents Chemother. 1974 Mar;5(3):255-67. doi: 10.1128/aac.5.3.255. PMID: 4599122; PMCID: PMC428957.

12: Fujimoto H, Kinoshita T, Suzuki H, Umezawa H. Studies on the mode of action of althiomycin. J Antibiot (Tokyo). 1970 Jun;23(6):271-5. doi: 10.7164/antibiotics.23.271. PMID: 4917791.

13: YAMAGUCHI H, NAKAYAMA Y, TAKEDA K, TAWARA K, MAEDA K, TAKEUCHI T, UMEZAWA H. A new antibiotic, althiomycin. J Antibiot (Tokyo). 1957 Sep;10(5):195-200. PMID: 13513511.