Hydroxystreptomycin | CAS#6835-00-3 | antibiotic

MedKoo Cat#: 461241 | Name: Hydroxystreptomycin

Description:

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

Hydroxystreptomycin is a new antibiotic from Streptomyces Griseocarneus.

Chemical Structure

Hydroxystreptomycin

CAS#6835-00-3

Theoretical Analysis

MedKoo Cat#: 461241

Name: Hydroxystreptomycin

CAS#: 6835-00-3

Chemical Formula: C21H39N7O13

Exact Mass: 597.2606

Molecular Weight: 597.57

Elemental Analysis: C, 42.21; H, 6.58; N, 16.41; O, 34.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Hydroxystreptomycin; Streptomycin C;

IUPAC/Chemical Name

1,1'-((1R,2R,3S,4R,5R,6S)-4-(((2R,3R,4R,5S)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-4-formyl-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine

InChi Key

OFNXOACBUMGOPC-HZYVHMACSA-N

InChi Code

InChI=1S/C21H39N7O13/c1-26-9-13(35)10(32)5(2-29)38-17(9)41-16-18(39-6(3-30)21(16,37)4-31)40-15-8(28-20(24)25)11(33)7(27-19(22)23)12(34)14(15)36/h4-18,26,29-30,32-37H,2-3H2,1H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1

SMILES Code

NC(N[C@@H]([C@H](O)[C@H]1O)[C@@H](O)[C@H](NC(N)=N)[C@H]1O[C@H](O[C@@H](CO)[C@]2(O)C=O)[C@@H]2O[C@H]3[C@@H](NC)[C@H](O)[C@H]([C@H](CO)O3)O)=N

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 597.57 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

1: Ono H, Crameri R, Hintermann G, Hütter R. Hydroxystreptomycin production and resistance in Streptomyces glaucescens. J Gen Microbiol. 1983 Feb;129(2):529-37. PubMed PMID: 6302205. 2: ARAI T, KURODA S, YAMAGISHI S, KATOH Y. A NEW HYDROXYSTREPTOMYCIN SOURCE, STREPTOMYCES SUBRUTILUS. J Antibiot (Tokyo). 1964 Jan;17:23-8. PubMed PMID: 14109821. 3: PITRE D. [Hydroxystreptomycin]. Farmaco Sci Tec. 1950 Nov-Dec;5(6):718-20. Undetermined Language. PubMed PMID: 14813298. 4: Vögtli M, Hütter R. Characterisation of the hydroxystreptomycin phosphotransferase gene (sph) of Streptomyces glaucescens: nucleotide sequence and promoter analysis. Mol Gen Genet. 1987 Jun;208(1-2):195-203. PubMed PMID: 3039305. 5: Ortseifen V, Winkler A, Albersmeier A, Wendler S, Pühler A, Kalinowski J, Rückert C. Complete genome sequence of the actinobacterium Streptomyces glaucescens GLA.O (DSM 40922) consisting of a linear chromosome and one linear plasmid. J Biotechnol. 2015 Jan 20;194:81-3. doi: 10.1016/j.jbiotec.2014.11.036. Epub 2014 Dec 9. PubMed PMID: 25499805. 6: BENEDICT RG, LINDENFELSER LA, STODOLA FH, TRAUFLER DH. Studies on Streptomyces griseocarneus and the production of hydroxystreptomycin. J Bacteriol. 1951 Oct;62(4):487-97. PubMed PMID: 14897819; PubMed Central PMCID: PMC386154. 7: Crameri R, Kieser T, Ono H, Sanchez J, Hütter R. Chromosomal instability in Streptomyces glaucescens: mapping of streptomycin-sensitive mutants. J Gen Microbiol. 1983 Feb;129(2):519-27. PubMed PMID: 6573433. 8: Beyer S, Distler J, Piepersberg W. The str gene cluster for the biosynthesis of 5'-hydroxystreptomycin in Streptomyces glaucescens GLA.0 (ETH 22794): new operons and evidence for pathway-specific regulation by StrR. Mol Gen Genet. 1996 Apr 10;250(6):775-84. PubMed PMID: 8628239. 9: Beyer S, Mayer G, Piepersberg W. The StrQ protein encoded in the gene cluster for 5'-hydroxystreptomycin of Streptomyces glaucescens GLA.0 is a alpha-D-glucose-1-phosphate cytidylyltransferase (CDP-D-glucose synthase). Eur J Biochem. 1998 Dec 15;258(3):1059-67. PubMed PMID: 9990325. 10: GRUNDY WE, WHITMAN AL, HANES ME, SYLVESTER JC. A study of streptomyces NA232-M1 and hydroxystreptomycin. Antibiot Chemother (Northfield). 1951 Aug;1(5):309-17. PubMed PMID: 24541678. 11: KLEIN D, PRAMER D. Bacterial dissimilation of streptomycin. J Bacteriol. 1961 Oct;82:505-10. PubMed PMID: 14456730; PubMed Central PMCID: PMC279198. 12: Hintermann G, Crameri R, Vögtli M, Hütter R. Streptomycin-sensitivity in Streptomyces glaucescens is due to deletions comprising the structural gene coding for a specific phosphotransferase. Mol Gen Genet. 1984;196(3):513-20. PubMed PMID: 6094980. 13: Crameri R, Hintermann G, Hütter R, Kieser T. Tyrosinase activity in Streptomyces glaucescens is controlled by three chromosomal loci. Can J Microbiol. 1984 Aug;30(8):1058-67. PubMed PMID: 6437655. 14: Schurter W, Kissling-Abderhalden M, Leisinger T. Glaucescin, a bacteriocin-like substance from Streptomyces glaucescens. J Gen Microbiol. 1979 Aug;113(2):243-53. PubMed PMID: 512635. 15: Distler J, Braun C, Ebert A, Piepersberg W. Gene cluster for streptomycin biosynthesis in Streptomyces griseus: analysis of a central region including the major resistance gene. Mol Gen Genet. 1987 Jun;208(1-2):204-10. PubMed PMID: 3039306. 16: Weber W, Zähner H, Siebers J, Schröder K, Zeeck A. [Metabolic products of microorganisms. 175. Tetracenomycin C (author's transl)]. Arch Microbiol. 1979 May;121(2):111-6. German. PubMed PMID: 485765.