Althiomycin | CAS#12656-40-5 | antibiotic

MedKoo Cat#: 592716 | Name: Althiomycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Althiomycin

CAS#12656-40-5

Theoretical Analysis

MedKoo Cat#: 592716

Name: Althiomycin

CAS#: 12656-40-5

Chemical Formula: C16H17N5O6S2

Exact Mass: 439.0620

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
1mg	USD 150.00	Ready to ship
5mg	USD 450.00	Ready to ship
10mg	USD 750.00	Ready to ship
25mg	USD 1,650.00	Ready to ship
50mg	USD 2,950.00	Ready to ship

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#YXM200717

QC Data

View QC data: current batch, Lot#YXM200717

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

A thiazole antibiotic.

In vitro activity:

TBD

In vivo activity:

TBD

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.

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

Formulation protocol:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: Moradi A, Yaghoubi-Avini M, Wink J. Isolation of Nannocystis species from Iran and exploring their natural products. Arch Microbiol. 2022 Jan 7;204(2):123. doi: 10.1007/s00203-021-02738-0. PMID: 34994917. 9: 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. 10: 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 (Reading). 2014 Aug;160(Pt 8):1609-1617. doi: 10.1099/mic.0.078576-0. Epub 2014 May 20. PMID: 24847000; PMCID: PMC4117218. 11: 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. 12: 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. 13: 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. 14: 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. 15: Liu SW, Jadambaa N, Nikandrova AA, Osterman IA, Sun CH. Exploring the Diversity and Antibacterial Potentiality of Cultivable Actinobacteria from the Soil of the Saxaul Forest in Southern Gobi Desert in Mongolia. Microorganisms. 2022 May 9;10(5):989. doi: 10.3390/microorganisms10050989. PMID: 35630432; PMCID: PMC9147431.