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Chemical Compound Review:

Valienamine (1S,4S,5S,6R)-4-amino-2...

Synonyms: CHEMBL1230806, SureCN3960550, CHEBI:40504, KST-1A4953, CTK4H9548, ...

Hyun, C.G. et al., Takeuchi, M. et al., Chen, X. et al., Stratmann, A. et al., Zheng, Y.G. et al.

Zheng, Shentu, Shen,

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Disease relevance of Valienamine

We examined the inhibitory effect of three pseudo-aminosugars (validamine, valienamine, and valiolamine), which were isolated from the broth of Streptomyces hygroscopicus, on the oligosaccharide-processing glucosidases I and II involved in glycoprotein biosynthesis in rat liver [1].
As these metabolites, some of which contain valienamine, are among the most potent antidiabetic agents thus far discovered, the molecular detection of specific metabolite-producing actinomycetes may prove a crucial step in current attempts to expand the scope and diversity of natural-product discovery [2].

High impact information on Valienamine

The cyclization product, 2-epi-5-epi-valiolone ((2S,3S,4S,5R)-5-(hydroxymethyl)cyclohexanon-2,3,4,5-tetrol), is a precursor of the valienamine moiety of acarbose [3].
Valienamine was found to be potent, competitive reversible inhibitor of porcine small intestinal sucrase in vitro with an IC50 value of 1.17 x 10(-3)M [4].
A reversed-phase high-performance liquid chromatography method for the quantitative analysis of valienamine in the microbial degradation of validamycin A, using a procedure for pre-column derivatization of valienamine with p-nitrofluorobenzene is described [5].

References

Inhibitory effect of pseudo-aminosugars on oligosaccharide glucosidases I and II and on lysosomal alpha-glucosidase from rat liver. Takeuchi, M., Kamata, K., Yoshida, M., Kameda, Y., Matsui, K. J. Biochem. (1990) [Pubmed]
Molecular detection of alpha-glucosidase inhibitor-producing actinomycetes. Hyun, C.G., Kim, S.Y., Hur, J.H., Seo, M.J., Suh, J.W., Kim, S.O. J. Microbiol. (2005) [Pubmed]
The AcbC protein from Actinoplanes species is a C7-cyclitol synthase related to 3-dehydroquinate synthases and is involved in the biosynthesis of the alpha-glucosidase inhibitor acarbose. Stratmann, A., Mahmud, T., Lee, S., Distler, J., Floss, H.G., Piepersberg, W. J. Biol. Chem. (1999) [Pubmed]
Inhibition of porcine small intestinal sucrase by valienamine. Zheng, Y.G., Shentu, X.P., Shen, Y.C. Journal of enzyme inhibition and medicinal chemistry. (2005) [Pubmed]
Quantitative analysis of valienamine in the microbial degradation of validamycin A after derivatization with p-nitrofluorobenzene by reversed-phase high-performance liquid chromatography. Chen, X., Zheng, Y., Shen, Y. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2005) [Pubmed]

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