Valiolamine | 83465-22-9 | Alpha-glucosidase inhibitor

MedKoo Cat#: 208058 | Name: Valiolamine

Description:

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

Valiolamine is a potent alpha-glucosidase inhibitor.

Chemical Structure

Valiolamine

CAS#83465-22-9

Theoretical Analysis

MedKoo Cat#: 208058

Name: Valiolamine

CAS#: 83465-22-9

Chemical Formula: C7H15NO5

Exact Mass: 193.0950

Molecular Weight: 193.20

Elemental Analysis: C, 43.52; H, 7.83; N, 7.25; O, 41.41

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

Valiolamine

IUPAC/Chemical Name

(1S,2S,3R,4S,5S)-5-amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol

InChi Key

VDLOJRUTNRJDJO-ZYNSJIGGSA-N

InChi Code

InChI=1S/C7H15NO5/c8-3-1-7(13,2-9)6(12)5(11)4(3)10/h3-6,9-13H,1-2,8H2/t3-,4-,5+,6-,7-/m0/s1

SMILES Code

OC[C@@]1(O)C[C@H](N)[C@H](O)[C@@H](O)[C@@H]1O

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 193.20 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: Karade SS, Hill ML, Kiappes JL, Manne R, Aakula B, Zitzmann N, Warfield KL, Treston AM, Mariuzza RA. N-Substituted Valiolamine Derivatives as Potent Inhibitors of Endoplasmic Reticulum α-Glucosidases I and II with Antiviral Activity. J Med Chem. 2021 Dec 23;64(24):18010-18024. doi: 10.1021/acs.jmedchem.1c01377. Epub 2021 Dec 6. PMID: 34870992. 2: Bin BH, Joo YH, Lee AY, Shin SS, Cho EG, Lee TR. Novel inhibitory effect of N-(2-hydroxycyclohexyl)valiolamine on melanin production in a human skin model. Int J Mol Sci. 2014 Jul 9;15(7):12188-95. doi: 10.3390/ijms150712188. PMID: 25007819; PMCID: PMC4139837. 3: Bin BH, Seo J, Yang SH, Lee E, Choi H, Kim KH, Cho EG, Lee TR. Novel inhibitory effect of the antidiabetic drug voglibose on melanogenesis. Exp Dermatol. 2013 Aug;22(8):541-6. doi: 10.1111/exd.12195. PMID: 23879813. 4: Wang C, Sun Y, Wen Q, Wang G, Wang Y, Qu Q, Yang G, Hu X. Novel reagents for quantitative analysis of valiolamine in biological samples by high-performance liquid chromatography with pre-column UV derivatization. Talanta. 2010 Jun 15;81(4-5):1613-8. doi: 10.1016/j.talanta.2010.03.011. Epub 2010 Mar 19. PMID: 20441947. 5: Li H, Lee JR, Nguyen do QA, Kim SB, Seo YG, Chang YK, Hong SK, Moon MH, Chung IY, Kim CJ. Quantitative analysis of valiolamine through pre-column derivatization with phenylisocyanate using high-performance liquid chromatography with UV detection: selection of reagent, identification of derivative and optimization of derivatization conditions. J Pharm Biomed Anal. 2009 May 1;49(4):957-63. doi: 10.1016/j.jpba.2009.02.020. Epub 2009 Feb 27. PMID: 19303235. 6: Ogawa S, Kanto M. Design and synthesis of 5a-carbaglycopyranosylamime glycosidase inhibitors. Curr Top Med Chem. 2009;9(1):58-75. doi: 10.2174/156802609787354324. PMID: 19199996. 7: Shing TK, Cheng HM. Intramolecular direct aldol reactions of sugar diketones: syntheses of valiolamine and validoxylamine G. Org Lett. 2008 Sep 18;10(18):4137-9. doi: 10.1021/ol801889n. Epub 2008 Aug 26. PMID: 18729372. 8: Ogawa S, Kanto M. Synthesis of valiolamine and some precursors for bioactive carbaglycosylamines from (-)-vibo-quercitol produced by biogenesis of myo- inositol. J Nat Prod. 2007 Mar;70(3):493-7. doi: 10.1021/np068069t. Epub 2007 Mar 9. PMID: 17346079. 9: Andriuzzi O, Gravier-Pelletier C, Bertho G, Prangé T, Le Merrer Y. Synthesis and glycosidase inhibitory activity of new hexa-substituted C8-glycomimetics. Beilstein J Org Chem. 2005 Oct 7;1(1):12. doi: 10.1186/1860-5397-1-12. PMID: 16542023; PMCID: PMC1399460. 10: Chen X, Zheng Y, Shen Y. Voglibose (Basen, AO-128), one of the most important alpha-glucosidase inhibitors. Curr Med Chem. 2006;13(1):109-16. doi: 10.2174/092986706789803035. PMID: 16457643. 11: Ogawa S, Ohishi Y, Asada M, Tomoda A, Takahashi A, Ooki Y, Mori M, Itoh M, Korenaga T. Convenient synthesis of (+)-valiolamine and (-)-1-epi-valiolamine from (-)-vibo-quercitol. Org Biomol Chem. 2004 Mar 21;2(6):884-9. doi: 10.1039/b314795a. Epub 2004 Feb 18. PMID: 15007418. 12: Arakawa K, Bowers SG, Michels B, Trin V, Mahmud T. Biosynthetic studies on the alpha-glucosidase inhibitor acarbose: the chemical synthesis of isotopically labeled 2-epi-5-epi-valiolone analogs. Carbohydr Res. 2003 Sep 26;338(20):2075-82. doi: 10.1016/s0008-6215(03)00315-x. PMID: 14505874. 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. doi: 10.1021/ja003643n. PMID: 11456959. 14: Ohtake H, Ikegami S. Facile ring transformation from gluconolactone to cyclitol derivative via spiro sugar ortho ester. Org Lett. 2000 Feb 24;2(4):457-60. doi: 10.1021/ol9913035. PMID: 10814350. 15: Uribe M, Morán S, de la Mora G. Manipulaciones dietéticas en pacientes con encefalopatía hepática [Dietetic manipulations in patients with hepatic encephalopathy]. Rev Gastroenterol Mex. 1994 Apr-Jun;59(2 Suppl):74-8. Spanish. PMID: 7916474. 16: 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. doi: 10.1248/cpb.38.1970. PMID: 2268898. 17: 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. doi: 10.1093/oxfordjournals.jbchem.a123160. PMID: 2229010. 18: Horii S, Fukase H, Matsuo T, Kameda Y, Asano N, Matsui K. Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents. J Med Chem. 1986 Jun;29(6):1038-46. doi: 10.1021/jm00156a023. PMID: 3519969. 19: Kameda Y, Asano N, Takeuchi M, Yamaguchi T, Matsui K, Horii S, Fukase H. Epivaliolamine and deoxyvalidamine, new pseudo-aminosugars produced by Streptomyces hygroscopicus. J Antibiot (Tokyo). 1985 Dec;38(12):1816-8. doi: 10.7164/antibiotics.38.1816. PMID: 3912362. 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. doi: 10.7164/antibiotics.37.1301. PMID: 6392268.