Validamine

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

MedKoo CAT#: 525352

CAS#: 32780-32-8

Description: Validamine is a natural pseudo-aminosugar.


Price and Availability

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Validamine is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525352
Name: Validamine
CAS#: 32780-32-8
Chemical Formula: C7H15NO4
Exact Mass: 177.1001
Molecular Weight: 177.2
Elemental Analysis: C, 47.45; H, 8.53; N, 7.90; O, 36.12


Synonym: Validamine

IUPAC/Chemical Name: (1R,2S,3S,4S,6R)-4-Amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol

InChi Key: GSQYAWMREAXBHF-UOYQFSTFSA-N

InChi Code: InChI=1S/C7H15NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h3-7,9-12H,1-2,8H2/t3-,4+,5-,6+,7+/m1/s1

SMILES Code: O[C@H]1[C@H](O)[C@@H](O)[C@@H](N)C[C@@H]1CO


Technical Data

Appearance:
White to off-white 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).

Harmonized System Code:
293490


References

1: Schalli M, Wolfsgruber A, Gonzalez Santana A, Tysoe C, Fischer R, Stütz AE, Thonhofer M, Withers SG. C-5a-substituted validamine type glycosidase inhibitors. Carbohydr Res. 2017 Feb 22;440-441:1-9. doi: 10.1016/j.carres.2017.01.006. Epub 2017 Jan 13. PubMed PMID: 28135569.

2: Hugelshofer CL, Mellem KT, Myers AG. Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine. Org Lett. 2013 Jun 21;15(12):3134-7. doi: 10.1021/ol401337p. Epub 2013 Jun 7. PubMed PMID: 23746325; PubMed Central PMCID: PMC3884032.

3: Xue YP, Qin JW, Wang YJ, Wang YS, Zheng YG. Enhanced production of acarbose and concurrently reduced formation of impurity c by addition of validamine in fermentation of Actinoplanes utahensis ZJB-08196. Biomed Res Int. 2013;2013:705418. doi: 10.1155/2013/705418. Epub 2013 Jan 22. PubMed PMID: 23484146; PubMed Central PMCID: PMC3581085.

4: Asamizu S, Yang J, Almabruk KH, Mahmud T. Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis. J Am Chem Soc. 2011 Aug 10;133(31):12124-35. doi: 10.1021/ja203574u. Epub 2011 Jul 18. PubMed PMID: 21766819; PubMed Central PMCID: PMC3162038.

5: Ogawa S, Kanto M. Design and synthesis of 5a-carbaglycopyranosylamime glycosidase inhibitors. Curr Top Med Chem. 2009;9(1):58-75. Review. PubMed PMID: 19199996.

6: Xu H, Yang J, Bai L, Deng Z, Mahmud T. Genetically engineered production of 1,1'-bis-valienamine and validienamycin in Streptomyces hygroscopicus and their conversion to valienamine. Appl Microbiol Biotechnol. 2009 Jan;81(5):895-902. doi: 10.1007/s00253-008-1711-z. Epub 2008 Sep 27. PubMed PMID: 18820907; PubMed Central PMCID: PMC2610235.

7: Wang Y, Bennet AJ. A potent bicyclic inhibitor of a family 27 alpha-galactosidase. Org Biomol Chem. 2007 Jun 7;5(11):1731-8. Epub 2007 Apr 30. PubMed PMID: 17520141.

8: Xue YP, Zheng YG, Chen XL, Shen YC. Quantitative determination of valienamine and validamine by thin-layer chromatography. J Chromatogr Sci. 2007 Feb;45(2):87-90. PubMed PMID: 17425137.

9: Rassu G, Auzzas L, Zambrano V, Burreddu P, Pinna L, Battistini L, Zanardi F, Casiraghi G. Variable strategy toward carbasugars and relatives. 6. Diastereoselective synthesis of 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose. J Org Chem. 2004 Mar 5;69(5):1625-8. PubMed PMID: 14987021.

10: Ogawa S, Watanabe M, Maruyama A, Hisamatsu S. Synthesis of an alpha-fucosidase inhibitor, 5a-carba-beta-L-fucopyranosylamine, and fucose-type alpha- and beta-DL-valienamine unsaturated derivatives. Bioorg Med Chem Lett. 2002 Mar 11;12(5):749-52. PubMed PMID: 11858994.

11: Ogawa S, Sekura R, Maruyama A, Odagiri T, Yuasa H, Hashimoto H. Synthesis and evaluation of alpha-fucosidase inhibitory activity of 5a-carba-alpha-L-fucopyranose and alpha-DL-fucopyranosylamine. Carbohydr Lett. 2000;4(1):13-20. PubMed PMID: 11469333.

12: Mahmud T, Xu J, Choi YU. Synthesis of 5-epi-[6-(2)H(2)]valiolone and stereospecifically monodeuterated 5-epi-valiolones: exploring the steric course of 5-epi-valiolone dehydratase in validamycin A biosynthesis. J Org Chem. 2001 Jul 27;66(15):5066-73. PubMed PMID: 11463258.

13: Dong H, Mahmud T, Tornus I, Lee S, Floss HG. Biosynthesis of the validamycins: identification of intermediates in the biosynthesis of validamycin A by Streptomyces hygroscopicus var. limoneus. J Am Chem Soc. 2001 Mar 28;123(12):2733-42. PubMed PMID: 11456959.

14: Rassu G, Auzzas L, Pinna L, Battistini L, Zanardi F, Marzocchi L, Acquotti D, Casiraghi G. Variable strategy toward carbasugars and relatives. 1. Stereocontrolled synthesis of pseudo-beta-D-gulopyranose, pseudo-beta-D-xylofuranose, (pseudo-beta-D-gulopyranosyl)amine, and (pseudo-beta-D-xylofuranosyl)amine. J Org Chem. 2000 Oct 6;65(20):6307-18. PubMed PMID: 11052072.

15: Tatsuta K, Mukai H, Takahashi M. Novel synthesis of natural pseudo-aminosugars, (+)-valienamine and (+)-validamine. J Antibiot (Tokyo). 2000 Apr;53(4):430-5. PubMed PMID: 10866227.

16: Kameda Y, Kawashima K, Takeuchi M, Ikeda K, Asano N, Matsui K. Preparation and biological activity of manno- and galacto-validamines, new 5a-carba-glycosylamines as alpha-glycosidase inhibitors. Carbohydr Res. 1997 May 16;300(3):259-64. PubMed PMID: 9202410.

17: Furumoto T, Kameda Y, Matsui K. Enzymatic synthesis of glucoside derivatives of validamine and valienamine. Chem Pharm Bull (Tokyo). 1992 Jul;40(7):1871-5. PubMed PMID: 1394706.

18: Takeuchi M, Takai N, Asano N, Kameda Y, Matsui K. Inhibitory effect of validamine, valienamine and valiolamine on activities of carbohydrases in rat small intestinal brush border membranes. Chem Pharm Bull (Tokyo). 1990 Jul;38(7):1970-2. PubMed PMID: 2268898.

19: Takeuchi M, Kamata K, Yoshida M, Kameda Y, Matsui K. Inhibitory effect of pseudo-aminosugars on oligosaccharide glucosidases I and II and on lysosomal alpha-glucosidase from rat liver. J Biochem. 1990 Jul;108(1):42-6. PubMed PMID: 2229010.

20: Kameda Y, Asano N, Yoshikawa M, Takeuchi M, Yamaguchi T, Matsui K, Horii S, Fukase H. Valiolamine, a new alpha-glucosidase inhibiting aminocyclitol produced by Streptomyces hygroscopicus. J Antibiot (Tokyo). 1984 Nov;37(11):1301-7. PubMed PMID: 6392268.