| Revision as of 13:33, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463496638 of page Acarviosin for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 13:11, 28 April 2023 edit LegionMammal978 (talk | contribs)Extended confirmed users7,894 edits move systematic name |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 477363643 |
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| ImageFile = Acarviosin.svg |
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| ImageFile = Acarviosin.svg |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| IUPACName = Methyl 4,6-dideoxy-4-{amino}-α-<small>D</small>-glucopyranoside |
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| IUPACName = Methyl 4,6-dideoxy-4-{amino}-α-<small>D</small>-glucopyranoside |
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| SystematicName = (1''R'',2''R'',3''S'',6''R'')-4-(Hydroxymethyl)-6-<nowiki/>{amino}cyclohex-4-ene-1,2,3-triol |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 80943-41-5 --> |
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| CASNo = 80943-41-5 |
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| CASNo_Ref = {{cascite|correct|}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| PubChem = 3083346 |
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| PubChem = 3083346 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2340579 |
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| ChemSpiderID = 2340579 |
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| SMILES = O2(O)(N1/C=C(/CO)(O)(O)1O)(O2OC)C |
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| SMILES = O2(O)(N1/C=C(/CO)(O)(O)1O)(O2OC)C |
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| 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/s1 |
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| 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/s1 |
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| InChIKey = KFHKERRGDZTZQJ-HHHVGSORBI |
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| InChIKey = KFHKERRGDZTZQJ-HHHVGSORBI |
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| StdInChI = 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/s1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KFHKERRGDZTZQJ-HHHVGSORSA-N |
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| StdInChI = 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/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KFHKERRGDZTZQJ-HHHVGSORSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=14|H=25|N=1|O=8 |
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| C=14 | H=25 | N=1 | O=8 |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = 1.488 g/mL |
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| MeltingPt = |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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'''Acarviosin''' is a sugar composed of ] linked to a 4-amino-4,6-dideoxy-<small>D</small>-glucopyranose. Acarviosin is part of the potent ] inhibitor ] and its derivatives. Acarviosin is a product of the degradation of acarbose by ], the glycoside hydrolase from gut bacteria ''Lactobacillus plantarum'' is able to hydrolyze acarbose to maltose and acarviosin.<ref>{{Cite journal|last1=Jang|first1=Myoung-Uoon|last2=Kang|first2=Hye-Jeong|last3=Jeong|first3=Chang-Ku|last4=Kang|first4=Yewon|last5=Park|first5=Ji-Eun|last6=Kim|first6=Tae-Jip|date=2018-02-01|title=Functional expression and enzymatic characterization of Lactobacillus plantarum cyclomaltodextrinase catalyzing novel acarbose hydrolysis|url=https://doi.org/10.1007/s12275-018-7551-3|journal=Journal of Microbiology|language=en|volume=56|issue=2|pages=113–118|doi=10.1007/s12275-018-7551-3|pmid=29392561 |s2cid=2660911 |issn=1976-3794}}</ref> 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 ]s <ref>{{Cite journal |
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| last1 = Zhong | first1 = D. |
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| last2 = Si | first2 = D. |
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| last3 = He | first3 = W. |
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| last4 = Zhao | first4 = L. |
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| last5 = Xu | first5 = Q. |
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| title = Structural revision of isovalertatins M03, M13, and M23 isolated from the culture of Streptomyces luteogriseus |
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| journal = Carbohydrate Research |
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| volume = 331 |
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| issue = 1 |
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| pages = 69–75 |
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| year = 2001 |
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| pmid = 11284506 | doi=10.1016/s0008-6215(01)00006-4 |
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}}</ref> and ]s <ref>{{Cite journal |
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| last1 = Si | first1 = D. |
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| last2 = Zhong | first2 = D. |
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| last3 = Xu | first3 = Q. |
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| title = Two butylated aminooligosaccharides isolated from the culture filtrate of Streptomyces luteogriseus |
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| journal = Carbohydrate Research |
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| volume = 335 |
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| issue = 2 |
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| pages = 127–132 |
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| year = 2001 |
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| pmid = 11567643 |
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| doi=10.1016/s0008-6215(01)00218-x |
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}}</ref> from '']'' and longer ]s from '']''.<ref>{{Cite journal |
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| last1 = Geng | first1 = P. |
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| last2 = Qiu | first2 = F. |
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| last3 = Zhu | first3 = Y. |
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| last4 = Bai | first4 = G. |
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| title = Four acarviosin-containing oligosaccharides identified from Streptomyces coelicoflavus ZG0656 are potent inhibitors of α-amylase |
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| doi = 10.1016/j.carres.2008.01.020 |
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| journal = Carbohydrate Research |
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| volume = 343 |
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| issue = 5 |
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| pages = 882–892 |
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| year = 2008 |
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| pmid = 18294624 |
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| pmc = |
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}}</ref> |
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==References== |
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{{Reflist}} |
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