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Acarviosin

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Acarviosin
Names
IUPAC name Methyl 4,6-dideoxy-4-{amino}-α-D-glucopyranoside
Systematic IUPAC name (1R,2R,3S,6R)-4-(Hydroxymethyl)-6-{amino}cyclohex-4-ene-1,2,3-triol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H25NO8/c1-5-8(11(19)13(21)14(22-2)23-5)15-7-3-6(4-16)9(17)12(20)10(7)18/h3,5,7-21H,4H2,1-2H3/t5-,7-,8-,9+,10-,11+,12-,13-,14+/m1/s1Key: KFHKERRGDZTZQJ-HHHVGSORSA-N
  • InChI=1/C14H25NO8/c1-5-8(11(19)13(21)14(22-2)23-5)15-7-3-6(4-16)9(17)12(20)10(7)18/h3,5,7-21H,4H2,1-2H3/t5-,7-,8-,9+,10-,11+,12-,13-,14+/m1/s1Key: KFHKERRGDZTZQJ-HHHVGSORBI
SMILES
  • O2(O)(N1/C=C(/CO)(O)(O)1O)(O2OC)C
Properties
Chemical formula C14H25NO8
Molar mass 335.353 g·mol
Density 1.488 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. Acarviosin is a product of the degradation of acarbose by gut microbiota, the glycoside hydrolase from gut bacteria Lactobacillus plantarum is able to hydrolyze acarbose to maltose and acarviosin. 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 and butytatins from Streptomyces luteogriseus and longer oligosaccharides from Streptomyces coelicoflavus.

References

  1. Jang, Myoung-Uoon; Kang, Hye-Jeong; Jeong, Chang-Ku; Kang, Yewon; Park, Ji-Eun; Kim, Tae-Jip (2018-02-01). "Functional expression and enzymatic characterization of Lactobacillus plantarum cyclomaltodextrinase catalyzing novel acarbose hydrolysis". Journal of Microbiology. 56 (2): 113–118. doi:10.1007/s12275-018-7551-3. ISSN 1976-3794. PMID 29392561. S2CID 2660911.
  2. 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.
  3. 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.
  4. 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.
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