Acarviosin

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Acarviosin
Acarviosin.svg
Names
IUPAC name
Methyl 4,6-dideoxy-4-{[(1R,4S,5R,6R)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}-α-D-glucopyranoside
Identifiers
3D model (JSmol)
ChemSpider
Properties
C14H25NO8
Molar mass 335.35 g·mol−1
Density 1.488 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acarviosin is a sugar composed of cyclohexitol linked to a 4-amino-4,6-dideoxy-D-glucopyranose. Acarviosin is part of the potent α-amylase inhibitor acarbose and its derivatives. The nitrogen atom binds to α-amylase more tightly than the natural substrate making it more potent than other inhibitors. Several other acarviosin-containing α-amylase inhibitors have been found in microbes including isovalertatins [1] and butytatins [2] from Streptomyces luteogriseus and longer oligosaccharides from Streptomyces coelicoflavus.[3]

References[edit]

  1. ^ Zhong, D.; Si, D.; He, W.; Zhao, L.; Xu, Q. (2001). "Structural revision of isovalertatins M03, M13, and M23 isolated from the culture of Streptomyces luteogriseus". Carbohydrate research. 331 (1): 69–75. doi:10.1016/s0008-6215(01)00006-4. PMID 11284506. 
  2. ^ Si, D.; Zhong, D.; Xu, Q. (2001). "Two butylated aminooligosaccharides isolated from the culture filtrate of Streptomyces luteogriseus". Carbohydrate research. 335 (2): 127–132. doi:10.1016/s0008-6215(01)00218-x. PMID 11567643. 
  3. ^ Geng, P.; Qiu, F.; Zhu, Y.; Bai, G. (2008). "Four acarviosin-containing oligosaccharides identified from Streptomyces coelicoflavus ZG0656 are potent inhibitors of α-amylase". Carbohydrate Research. 343 (5): 882–892. doi:10.1016/j.carres.2008.01.020. PMID 18294624.