Chemistry:Acarviosin
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| Names | |
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| 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
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| Systematic IUPAC name
(1R,2R,3S,6R)-4-(Hydroxymethyl)-6-{[(2R,3S,4S,5R,6S)-6-methoxy-2-methyl-4,5-dihydroxyoxan-3-yl]amino}cyclohex-4-ene-1,2,3-triol | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C14H25NO8 | |
| Molar mass | 335.353 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). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
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.[1] 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 [2] and butytatins [3] from Streptomyces luteogriseus and longer oligosaccharides from Streptomyces coelicoflavus.[4]
References
- ↑ 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" (in en). Journal of Microbiology 56 (2): 113–118. doi:10.1007/s12275-018-7551-3. ISSN 1976-3794. PMID 29392561. https://doi.org/10.1007/s12275-018-7551-3.
- ↑ 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.
- ↑ 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.
- ↑ 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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