MedKoo Cat#: 558068 | Name: Kanosamine

Description:

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

Kanosamine is an antifungal.

Chemical Structure

Kanosamine
Kanosamine
CAS#576-44-3

Theoretical Analysis

MedKoo Cat#: 558068

Name: Kanosamine

CAS#: 576-44-3

Chemical Formula: C6H13NO5

Exact Mass: 179.0800

Molecular Weight:

Elemental Analysis: C, 40.22; H, 7.31; N, 7.82; O, 44.65

Price and Availability

Size Price Availability Quantity
10mg USD 530.00
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Related CAS #
No Data
Synonym
3-Amino-3-deoxyglucose;
IUPAC/Chemical Name
D-Glucose, 3-amino-3-deoxy-
InChi Key
FOEXHEVNPRRHDY-SLPGGIOYSA-N
InChi Code
InChI=1S/C6H13NO5/c7-5(3(10)1-8)6(12)4(11)2-9/h1,3-6,9-12H,2,7H2/t3-,4+,5+,6+/m0/s1
SMILES Code
O=C[C@@H]([C@@H](N)[C@@H]([C@@H](CO)O)O)O
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 0.00 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
1: Vetter ND, Langill DM, Anjum S, Boisvert-Martel J, Jagdhane RC, Omene E, Zheng H, van Straaten KE, Asiamah I, Krol ES, Sanders DA, Palmer DR. A previously unrecognized kanosamine biosynthesis pathway in Bacillus subtilis. J Am Chem Soc. 2013 Apr 24;135(16):5970-3. doi: 10.1021/ja4010255. Epub 2013 Apr 15. PubMed PMID: 23586652. 2: van Straaten KE, Ko JB, Jagdhane R, Anjum S, Palmer DR, Sanders DA. The structure of NtdA, a sugar aminotransferase involved in the kanosamine biosynthetic pathway in Bacillus subtilis, reveals a new subclass of aminotransferases. J Biol Chem. 2013 Nov 22;288(47):34121-30. doi: 10.1074/jbc.M113.500637. Epub 2013 Oct 4. PubMed PMID: 24097983; PubMed Central PMCID: PMC3837154. 3: Guo J, Frost JW. Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom. J Am Chem Soc. 2002 Sep 11;124(36):10642-3. PubMed PMID: 12207504. 4: Janiak AM, Milewski S. Mechanism of antifungal action of kanosamine. Med Mycol. 2001 Oct;39(5):401-8. PubMed PMID: 12054050. 5: Milner JL, Silo-Suh L, Lee JC, He H, Clardy J, Handelsman J. Production of kanosamine by Bacillus cereus UW85. Appl Environ Microbiol. 1996 Aug;62(8):3061-5. PubMed PMID: 8702302; PubMed Central PMCID: PMC168096. 6: Arakawa K, Müller R, Mahmud T, Yu TW, Floss HG. Characterization of the early stage aminoshikimate pathway in the formation of 3-amino-5-hydroxybenzoic acid: the RifN protein specifically converts kanosamine into kanosamine 6-phosphate. J Am Chem Soc. 2002 Sep 11;124(36):10644-5. PubMed PMID: 12207505. 7: Shang H, Chen J, Handelsman J, Goodman RM. Behavior of pythium Torulosum zoospores during their interaction with tobacco roots and Bacillus cereus. Curr Microbiol. 1999 Apr;38(4):199-204. PubMed PMID: 10069854. 8: Tachibana M, Jung W, Schindler K, Schacht J. Are aminosugars ototoxic? Arch Otorhinolaryngol. 1981;230(2):103-7. PubMed PMID: 7295169. 9: Kevany BM, Rasko DA, Thomas MG. Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus. Appl Environ Microbiol. 2009 Feb;75(4):1144-55. doi: 10.1128/AEM.02518-08. Epub 2008 Dec 19. PubMed PMID: 19098220; PubMed Central PMCID: PMC2643575. 10: Sasaki K, Aizawa S, Satomi T, Akutsu H, Kawabata S, Momoki Y, Douros JD. Synthesis and antitumor activity of N-nitrosoureido derivatives of kanosamine. J Antibiot (Tokyo). 1980 May;33(5):517-9. PubMed PMID: 7429976. 11: Floss HG, Yu TW, Arakawa K. The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review. J Antibiot (Tokyo). 2011 Jan;64(1):35-44. doi: 10.1038/ja.2010.139. Epub 2010 Nov 17. Review. PubMed PMID: 21081954. 12: Silo-Suh LA, Stabb EV, Raffel SJ, Handelsman J. Target range of zwittermicin A, an aminopolyol antibiotic from Bacillus cereus. Curr Microbiol. 1998 Jul;37(1):6-11. PubMed PMID: 9625782. 13: Meyer zu Reckendorf W. A simple synthesis of 3-amino-3-deoxy-D-glucose (kanosamine). Angew Chem Int Ed Engl. 1966 Nov;5(11):967. PubMed PMID: 4959563. 14: Vetter ND, Palmer DR. Simultaneous Measurement of Glucose-6-phosphate 3-Dehydrogenase (NtdC) Catalysis and the Nonenzymatic Reaction of Its Product: Kinetics and Isotope Effects on the First Step in Kanosamine Biosynthesis. Biochemistry. 2017 Apr 11;56(14):2001-2009. doi: 10.1021/acs.biochem.7b00079. Epub 2017 Mar 29. PubMed PMID: 28353336. 15: Dolak LA, Castle TM, Dietz A, Laborde AL. 3-Amino-3-deoxyglucose produced by a Streptomyces sp. J Antibiot (Tokyo). 1980 Aug;33(8):900-1. PubMed PMID: 7429991. 16: Fusetani N, Ejima D, Matsunaga S, Hashimoto K, Itagaki K, Akagi Y, Taga N, Suzuki K. 3-Amino-3-deoxy-D-glucose: an antibiotic produced by a deep-sea bacterium. Experientia. 1987 Apr 15;43(4):464-5. PubMed PMID: 3569498. 17: Le Goffic F, Capmau ML, Tangy F, Caminade E. Have deoxystreptamine aminoglycoside antibiotics the same binding site on bacterial ribosomes? J Antibiot (Tokyo). 1980 Aug;33(8):895-9. PubMed PMID: 7000739. 18: Giuliano RM, Kasperowicz S. Synthesis of branched-chain sugars: a stereoselective route to sibirosamine, kansosamine, and vinelose from a common precursor. Carbohydr Res. 1988 Dec 1;183(2):277-85. PubMed PMID: 3214842. 19: Golets LM, Esipov SE, Fedorenko VA. [Metabolites produced by Streptomyces kanamyceticus mutants with impaired biosynthesis of kanamycin]. Antibiot Khimioter. 1997;42(4):8-11. Russian. PubMed PMID: 9182507. 20: Segal JA, Skolnick P. Polyamine-like actions of aminoglycosides and aminoglycoside derivatives at NMDA receptors. Eur J Pharmacol. 1998 Apr 24;347(2-3):311-7. PubMed PMID: 9653898.