메뉴 건너뛰기




Volumn 34, Issue 6, 2004, Pages 1125-1139

Synthesis of a Tetrasaccharide Related to the Repeating Unit of the Antigen from Shigella dysenteriae Type 9 in the Form of Its 2-(Trimethylsilyl)ethyl Glycoside

Author keywords

N iodosuccinimide; Shigella dysenteriae; Tetrasaccharide; Trifluoromethanesulfonic acid

Indexed keywords

2 (TRIMETHYLSILY)ETHYL GLYCOSIDE; BACTERIAL ANTIGEN; DISACCHARIDE; GALACTOSE; GLUCOSAMINE; GLYCOCONJUGATE; GLYCOSIDE; MANNOSE; N IODOSUCCINIMIDE; OLIGOSACCHARIDE; SILANE DERIVATIVE; SUCCINIMIDE DERIVATIVE; TETRASACCHARIDE; TRICHLOROACETIMIDIC ACID; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 1842428783     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120028645     Document Type: Article
Times cited : (2)

References (20)
  • 1
    • 0026705492 scopus 로고
    • Epidemiology of drug resistance: Implication for a post-antimicrobial era
    • Cohen, M.L. Epidemiology of drug resistance: Implication for a post-antimicrobial era. Science 1992, 257, 1050-1055.
    • (1992) Science , vol.257 , pp. 1050-1055
    • Cohen, M.L.1
  • 2
    • 0026748459 scopus 로고
    • Hypothesis for vaccine devolopment: Protective immunity to enteric diseases caused by nontyphoidal Salmonellae and Shigellae may be conferred by serum IgG antibodies to the O-specific polysaccharide of their lipopolysaccharides
    • Robbins, J.B.; Chu, C.; Schneerson, R. Hypothesis for vaccine devolopment: Protective immunity to enteric diseases caused by nontyphoidal Salmonellae and Shigellae may be conferred by serum IgG antibodies to the O-specific polysaccharide of their lipopolysaccharides. Clin. Inf. Dis. 1992, 15, 346-361.
    • (1992) Clin. Inf. Dis. , vol.15 , pp. 346-361
    • Robbins, J.B.1    Chu, C.2    Schneerson, R.3
  • 3
    • 0031882559 scopus 로고    scopus 로고
    • Synthetic Shigella vaccines: A carbohydrate protein conjugate with totally synthetic hexadecasaccharide haptens
    • Pozsgay, V. Synthetic Shigella vaccines: A carbohydrate protein conjugate with totally synthetic hexadecasaccharide haptens. Angew. Chem. Int. Ed. 1998, 37, 138-142.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 138-142
    • Pozsgay, V.1
  • 4
    • 0021105896 scopus 로고
    • Immunochemical studies on Shigella dysenteriae type 9 bacterial polysaccharide
    • Pal, J.; Basu, S.; Rao, C.V.N. Immunochemical studies on Shigella dysenteriae type 9 bacterial polysaccharide. Carbohydr. Res. 1983, 114, 123-135.
    • (1983) Carbohydr. Res. , vol.114 , pp. 123-135
    • Pal, J.1    Basu, S.2    Rao, C.V.N.3
  • 5
    • 0347478174 scopus 로고    scopus 로고
    • Synthesis of a blocked tetrasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 9 in the form of its methyl (R)-pyruvate ester and 2-(trimethylsilyl)ethyl glycoside
    • Roy, S.; Roy, N. Synthesis of a blocked tetrasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 9 in the form of its methyl (R)-pyruvate ester and 2-(trimethylsilyl)ethyl glycoside. J. Carbohydr. Chem. 2003, 22, 521-535.
    • (2003) J. Carbohydr. Chem. , vol.22 , pp. 521-535
    • Roy, S.1    Roy, N.2
  • 6
    • 0031777948 scopus 로고
    • Synthesis of tetrasaccharide repeating unit of the K-antigen from Klebsiella type 57
    • Sarbajna, S.; Roy, N. Synthesis of tetrasaccharide repeating unit of the K-antigen from Klebsiella type 57. Carbohydr. Res. 1988, 306, 401-407.
    • (1988) Carbohydr. Res. , vol.306 , pp. 401-407
    • Sarbajna, S.1    Roy, N.2
  • 7
    • 0001642223 scopus 로고
    • The preparation and synthetic utility of tert-butyldiphenylsilyl ethers
    • Hanessian, S.; Lavallee, P. The preparation and synthetic utility of tert-butyldiphenylsilyl ethers. Can. J. Chem. 1975, 53, 2975-2977.
    • (1975) Can. J. Chem. , vol.53 , pp. 2975-2977
    • Hanessian, S.1    Lavallee, P.2
  • 8
    • 0023050091 scopus 로고
    • Glycosylation of lactose: Synthesis of branched oligosaccharides involved in the biosynthesis of glycolipids having blood-group I activity
    • (a) Maranduba, A.; Veyriéres, A. Glycosylation of lactose: Synthesis of branched oligosaccharides involved in the biosynthesis of glycolipids having blood-group I activity. Carbohydr. Res. 1986, 151, 105-119;
    • (1986) Carbohydr. Res. , vol.151 , pp. 105-119
    • Maranduba, A.1    Veyriéres, A.2
  • 9
    • 0000884597 scopus 로고
    • Anwendung des trichloracetimidatverfahrens auf 2-desoxy-2-phthalimido-D-glucose-derivative. Synthese von oligosacchariden der "Core-Region" von O-glycoproteinen des mucin-types
    • (b) Grundler, G.; Schmidt, R.R. Anwendung des trichloracetimidatverfahrens auf 2-desoxy-2-phthalimido-D-glucose-derivative. Synthese von oligosacchariden der "Core-Region" von O-glycoproteinen des mucin-types. Carbohydr. Res. 1985, 135, 203-218.
    • (1985) Carbohydr. Res. , vol.135 , pp. 203-218
    • Grundler, G.1    Schmidt, R.R.2
  • 10
    • 0028186224 scopus 로고
    • Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method
    • Schmidt, R.R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
    • (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 21-123
    • Schmidt, R.R.1    Kinzy, W.2
  • 11
    • 0022636075 scopus 로고
    • New methods for the synthesis of glycosides and oligosaccharide-are there alternative to the Koenigs-Knorr?
    • Schmidt, R.R. New methods for the synthesis of glycosides and oligosaccharide-are there alternative to the Koenigs-Knorr? Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 212-235
    • Schmidt, R.R.1
  • 12
    • 0027676464 scopus 로고
    • Synthesis of di- to pentasaccharides related to the O-specific polysaccharide of Shigella dysenteriae type 1, and their nuclear magnetic resonance study
    • Posgay, V.; Coxon, B.; Yeh, H. Synthesis of di- to pentasaccharides related to the O-specific polysaccharide of Shigella dysenteriae type 1, and their nuclear magnetic resonance study. Bioorg. Med. Chem. 1993, 1, 237-257.
    • (1993) Bioorg. Med. Chem. , vol.1 , pp. 237-257
    • Posgay, V.1    Coxon, B.2    Yeh, H.3
  • 13
    • 0000836807 scopus 로고
    • Methyl 4,6-O-benzylidene α- and β-D-glucopyranoside via acetal exchange
    • Evans, M.E. Methyl 4,6-O-benzylidene α- and β -D-glucopyranoside via acetal exchange. In Methods Carbohydr. Chem. 1980, 8, 313-315.
    • (1980) Methods Carbohydr. Chem. , vol.8 , pp. 313-315
    • Evans, M.E.1
  • 14
    • 0027579802 scopus 로고
    • Acceptor-substrate recognition by N-acetylglucosaminyltransferase-V; Critical role of the 4"-hydroxyl group in β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → 6)-β-D-Glcp-OR
    • Kanie, O.; Crawley, S.C.; Palcic, M.M.; Hindsgaul, O. Acceptor-substrate recognition by N-acetylglucosaminyltransferase-V; Critical role of the 4"-hydroxyl group in β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → 6)-β-D-Glcp-OR. Carbohydr. Res. 1993, 243, 139-164.
    • (1993) Carbohydr. Res. , vol.243 , pp. 139-164
    • Kanie, O.1    Crawley, S.C.2    Palcic, M.M.3    Hindsgaul, O.4
  • 15
    • 33845278486 scopus 로고
    • 2-(Trimethylsilyl)ethyl glycosides. Synthesis, anomeric deblocking and transformation into 1,2-trans 1-O-acetyl sugars
    • Jansson, K.; Ahlfors, S.; Frejd, T.; Kihlberg, J.; Magnusson, G. 2-(Trimethylsilyl)ethyl glycosides. Synthesis, anomeric deblocking and transformation into 1,2-trans 1-O-acetyl sugars. J. Org. Chem. 1988, 53, 5629-5647.
    • (1988) J. Org. Chem. , vol.53 , pp. 5629-5647
    • Jansson, K.1    Ahlfors, S.2    Frejd, T.3    Kihlberg, J.4    Magnusson, G.5
  • 16
    • 0012473461 scopus 로고
    • Alkylation of monosaccharides using sodium hydride
    • Brimacombe, J.S. Alkylation of monosaccharides using sodium hydride. In Methods Carbohydr. Chem. 1972, 6, 376-378.
    • (1972) Methods Carbohydr. Chem. , vol.6 , pp. 376-378
    • Brimacombe, J.S.1
  • 17
    • 0002086064 scopus 로고
    • A novel reductive ring-opening of carbohydrate benzylidene acetals
    • Garegg, P.A.J.; Hultberg, H.; Walin, S. A novel reductive ring-opening of carbohydrate benzylidene acetals. Carbohydr. Res. 1982, 108, 97-101.
    • (1982) Carbohydr. Res. , vol.108 , pp. 97-101
    • Garegg, P.A.J.1    Hultberg, H.2    Walin, S.3
  • 18
    • 0034605825 scopus 로고    scopus 로고
    • Can preferential β-mannoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxide be reached with trichloroacetimidates?
    • Weingart, R.; Schmidt, R.R. Can preferential β-mannoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxide be reached with trichloroacetimidates? Tetrahedron Lett. 2000, 41, 8753-8758.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8753-8758
    • Weingart, R.1    Schmidt, R.R.2
  • 19
    • 0025125757 scopus 로고
    • Iodonium ion promoted reactions at the anomeric center. II. An efficient thioglycoside mediated approach towards the formation of 1,2-trans linked glycosides and glycosidic esters
    • Veeneman, G.H.; van Leeuwen, S.H.; van Boom, J.H. Iodonium ion promoted reactions at the anomeric center. II. An efficient thioglycoside mediated approach towards the formation of 1,2-trans linked glycosides and glycosidic esters. Tetrahedron Lett. 1990, 31, 1331-1334.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1331-1334
    • Veeneman, G.H.1    Van Leeuwen, S.H.2    Van Boom, J.H.3
  • 20
    • 0037470731 scopus 로고    scopus 로고
    • Synthesis of the pentasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 4 in the form of its methyl ester 2-(trimethyl silyl) ethyl glycoside
    • Mukhopadhyay, B.; Roy, N. Synthesis of the pentasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 4 in the form of its methyl ester 2-(trimethyl silyl) ethyl glycoside. Carbohydr. Res. 2003, 338, 589-596.
    • (2003) Carbohydr. Res. , vol.338 , pp. 589-596
    • Mukhopadhyay, B.1    Roy, N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.