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Volumn 121, Issue 4, 1999, Pages 734-753

Programmable one-pot oligosaccharide synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CARBOHYDRATE SYNTHESIS; COMPUTER PROGRAM; DATA BASE; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ASSAY; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0033518559     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982232s     Document Type: Article
Times cited : (828)

References (64)
  • 4
    • 0026445723 scopus 로고
    • (b) Lasky, L. A. Science 1992, 258, 964.
    • (1992) Science , vol.258 , pp. 964
    • Lasky, L.A.1
  • 9
    • 0008897689 scopus 로고
    • Garegg, P. J., Lindberg, A. A., Eds.; ACS Symposium Series 519; American Chemical Society; Washington, DC
    • (b) Meldal, M.; Mouritsen, S.; Bock, K. In Carbohydrate Antigens; Garegg, P. J., Lindberg, A. A., Eds.; ACS Symposium Series 519; American Chemical Society; Washington, DC, 1993; p 19.
    • (1993) Carbohydrate Antigens , pp. 19
    • Meldal, M.1    Mouritsen, S.2    Bock, K.3
  • 11
    • 0025102915 scopus 로고
    • For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
    • (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 823-839
    • Paulsen, H.1
  • 12
    • 0000198772 scopus 로고
    • For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
    • (1992) Chem. Rev. , vol.92 , pp. 1167-1195
    • Banoub, J.1
  • 13
    • 5244279498 scopus 로고
    • For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
    • (1993) Chem. Rev. , vol.93 , pp. 1503
    • Toshima, K.1    Tatsuta, K.2
  • 14
    • 0028186224 scopus 로고
    • For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
    • (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 21
    • Schmidt, R.R.1    Kinzy, W.2
  • 15
    • 0029739240 scopus 로고    scopus 로고
    • For recent review articles on oligosaccharide synthesis, see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-839. (b) Banoub, J. Chem. Rev. 1992, 92, 1167-1195. (c) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (d) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1380
    • Danishefsky, S.J.1    Bilodeau, M.T.2
  • 27
    • 37849189010 scopus 로고    scopus 로고
    • For a recent review on the synthesis and application of thioglycosides, see: Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
    • (1997) Adv. Carbohydr. Chem. Biochem. , vol.52 , pp. 179
    • Garegg, P.J.1
  • 44
    • 13044310031 scopus 로고    scopus 로고
    • note
    • A precise measurement with DMTST is difficult as its efficiency for the activation is lower than that of NIS: normally 4 equiv of DMTST is used for the glycosylation and the reaction is much slower than that of NIS. We observed that 2 equiv could be enough to complete a reaction with 1 equiv of thioglycoside within a certain time. For the competition reactions, the conditions were exactly the same as those with NIS-TfOH (see general procedure in Experimental Section), except that DMTST was taken as 2 mole equiv relative to the donors (each I mole equiv) and the reaction was continued for 3 h. This measurement can only be performed between donors with small reactivity differences.
  • 47
    • 13044284050 scopus 로고    scopus 로고
    • note
    • The elevated reactivity of N-Troc-protected glucosamines might be the result of the electron-donating property of the N-trichloroethoxycarbonyl group to stabilize the intermediate as shown in the following tentative mechanism. Research is underway to test the proposal.
  • 54
    • 13044289928 scopus 로고    scopus 로고
    • note
    • For example, in the synthesis of the lactoside 9 (see scheme below), in addition to the target disaccharide 9 (65%), the succinimide product 58 (15%) was also isolated as a byproduct.
  • 55
    • 13044305171 scopus 로고    scopus 로고
    • note
    • 48 (1776) 9 (6.9) 58 2.0 equiv 65% 15% The low reactivity of the 4-OH of glucoside 10 (RRV = 8.4), coupled with an increased reactivity of the transient intermediate cation derived from the initial reaction of galactoside 48 (RRV = 1776) with iodonium ion, could explain the formation of 57.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.