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Volumn 49, Issue 5, 2008, Pages 910-913

Iminosugar thioglycosides as glycosyl donors: a route to disaccharides with an iminosugar moiety

Author keywords

Glycosidations; Iminosugar disaccharides; Iminosugars; Thioglycosides

Indexed keywords

DISACCHARIDE; IMINOSUGAR; IMINOSUGAR THIOGLYCOSIDE DERIVATIVE; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

EID: 37649017844     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.160     Document Type: Article
Times cited : (5)

References (41)
  • 33
    • 37649017499 scopus 로고    scopus 로고
    • Fuentes, J.; Al Bujuq, N. R.; Pradera, M. A.; Gasch, C. Unpublished results communicated to the 'Eighth Tetrahedron Symposium' Berlin, Germany, June 2007, Communication P343.
  • 34
    • 37649010993 scopus 로고    scopus 로고
    • note
    • 8, 532.2910.
  • 35
    • 20444483055 scopus 로고    scopus 로고
    • note
    • For the molecular modelling calculations the force field TRIPOS was used as implemented in Sybyl 7.3 (Tripos Inc.). The starting structure was built with a ring puckering corresponding to a skewed boat conformation, as it was the only ring conformation in qualitative agreement with the experimental J-couplings, and, at the same time, showing the largest number of bulky exocyclic groups in the most stable equatorial or isoclinal orientations. The exocyclic torsions were optimized by determining the energy minimum in torsional energy maps with 60° increments (gridsearch module in Sybyl). Gasteiger-Hückel atomic partial charges were used and the energy minimization steps in all the calculations consisted in 1000 conjugated-gradients maximum iterations, an energy gradient limit of 0.01 Kcal/mol A, using a distance-dependent dielectric constant of 1·r, and a non-bonded cutoff of 8 A. Energy minimization led to significantly improved agreement between experimental and theoretical J-couplings. Theoretical distances were measured on the energy minimum, and the J-couplings were obtained using the Haasnoot-Altona empirical equation (Haasnoot, C. A. G.; De Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792). Any molecular model with an inverted configuration at C-2 was unable to predict the set of exclusive NOEs described in the discussion of results.
  • 36
    • 0023656051 scopus 로고
    • Compound 10 was a commercial product. For the preparation of 11, see:
    • Compound 10 was a commercial product. For the preparation of 11, see:. Bernotas R.C., Pezzone M.A., and Ganem B. Carbohydr. Res. 167 (1987) 305-311
    • (1987) Carbohydr. Res. , vol.167 , pp. 305-311
    • Bernotas, R.C.1    Pezzone, M.A.2    Ganem, B.3
  • 41
    • 37649020395 scopus 로고    scopus 로고
    • note
    • 13Na, 714.3102.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.