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Volumn 55, Issue 48, 2016, Pages 14978-14982

Structural Snapshots for Mechanism-Based Inactivation of a Glycoside Hydrolase by Cyclopropyl Carbasugars

Author keywords

carbocycles; enzyme mechanisms; glycoside hydrolases; inhibitors; X ray crystallography

Indexed keywords

CORROSION INHIBITORS; HYDROLASES; PLANTS (BOTANY); SUGARS;

EID: 84995802994     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201607431     Document Type: Article
Times cited : (29)

References (32)
  • 12
    • 85043835422 scopus 로고    scopus 로고
    • We have based the name for conformations of our carbosugar analogues on carbohydrate conformational nomenclature (see Ref. [8]), with the pseudo-anomeric carbon being assigned as atom number 1
    • We have based the name for conformations of our carbosugar analogues on carbohydrate conformational nomenclature (see Ref. [8]), with the pseudo-anomeric carbon being assigned as atom number 1.
  • 14
    • 85043796458 scopus 로고    scopus 로고
    • For a glycopyranosylium ion where the conformational restriction (double bond) is between C1 and O5, the two low-energy half-chairs are, H, H, (C2-C1-O5-C5 are co-planar). While in compound 1, where the conformational restriction (cyclopropyl ring) is located at the positions corresponding to C5 and O5 in a carbohydrate (quarternary and tertiary cyclopropyl carbons), the two accessible half-chair conformations are now, H, H
    • 3.
  • 19
    • 85043798179 scopus 로고    scopus 로고
    • This aldehyde can be made from diethyl malonate in three steps; full details can be found in the Supporting Information
    • This aldehyde can be made from diethyl malonate in three steps; full details can be found in the Supporting Information.
  • 21
    • 84995761200 scopus 로고    scopus 로고
    • Angew. Chem. 2015, 127, 15649;
    • (2015) Angew. Chem. , vol.127 , pp. 15649
  • 24
    • 85043804086 scopus 로고    scopus 로고
    • Aldehyde 6 could be prepared on a more than 50 g scale from diethylmalonate; see the Supporting Information for experimental details
    • Aldehyde 6 could be prepared on a more than 50 g scale from diethylmalonate; see the Supporting Information for experimental details.
  • 29
    • 85043802397 scopus 로고    scopus 로고
    • Rigorous exclusion of water was necessary to avoid the insertion the rhodium-carbenoid into an O−H bond of water
    • Rigorous exclusion of water was necessary to avoid the insertion the rhodium-carbenoid into an O−H bond of water.
  • 30
    • 85099673278 scopus 로고    scopus 로고
    • The use of catalytic Rh, (octanoate), or Rh, (caprolactam), for this reaction gave similar results, while CuI, Rh, (heptafluorobutyrate), Pd(OAc), proved to be inferior catalysts
    • 2 proved to be inferior catalysts.
  • 31
    • 85043823449 scopus 로고    scopus 로고
    • We estimate that we would have observed a 5 % return of enzyme activity
    • We estimate that we would have observed a 5 % return of enzyme activity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.