Properties of a synthetic antigen related to the human blood-group Lewis a

Lemieux, R. U.; Bundle, David R.; Baker, D.

doi:10.1021/ja00847a035

Cited by 310 publications

(86 citation statements)

References 18 publications

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“…Thus, glycosidation of the alcohols 5 and 65, derived from kaurenoic acid (1), with α-D-(+)-glucose derivatives, under the Koenigs-Knorr reaction conditions was carried out [163][164][165]. In spite of the disadvantage of this method requiring heavy metals as promoters of the reaction, it usually gives the highest global yield in the chemical synthesis of the glycosides [101].…”

Section: Synthesis Of Kaurane Glycosidesmentioning

confidence: 99%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed. Molecules 2007, 12 456

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Section: Synthesis Of Kaurane Glycosidesmentioning

confidence: 99%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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“…The molecular basis for the binding of pili to uroepithelium was assessed -with antireceptor antibodies by a technique previously employed to localize the Lewis blood group antigens in tissues (25)(26)(27). Syn Man-Man and Syn Gal-Gal were chemically synthesized and found to bind MS and Gal-Gal pili preparations, respectively (13, our Table I).…”

Section: Ggp+ Detected By Specific Antibody In the ------------------mentioning

confidence: 99%

Molecular basis of Escherichia coli colonization of the upper urinary tract in BALB/c mice. Gal-Gal pili immunization prevents Escherichia coli pyelonephritis in the BALB/c mouse model of human pyelonephritis.

O’Hanley¹,

Lark²,

Falkow³

et al. 1985

J. Clin. Invest.

212

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“…Were we report the preparation of the 3 possible subterminally phosphorylated oligosaccharides 2, 3, and 4. These structures were prepared as their 8-methoxycarbonyloctyl glycosides (10) to allow the preparation of synthetic glycoconjugates (11) for use in a study (12) of the intracellular transport of lysosomal enzymes.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of the subterminally 6-O-phosphorylated trimannosides found on carbohydrate chains of lysosomal enzymes

Srivastava¹,

Hindsgaul²

1986

Can. J. Chem.

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OM. P. SRIVASTAVA and OLE HINDSGAUL. Can. J . Chem. 64, 2324Chem. 64, (1986. The three possible subterminally 6-0-phosphorylated trimannosides (2-4) found on the asparagine-linked carbohydrate chains of lysosomal enzymes have been chemically synthesized as their 8-methoxycarbonyloctyl glycosides, R = (CH2)8COOCH3. The key step in the syntheses involves glycosylation of suitably protected a-D-mannopyranosides 5-7 with the phosphorylated mannobiosyl donor 2-0-(2,3,4,6-tetra-0-acetyl-a-~-mannopyranosyl)-3,4-di-0-benzyl-6-0-diphenylphosphoryl-a-D-mannopyranosyl chloride (141, which produced mixtures of a-and P-linked trisaccharidic products.Compounds 2 ( a~M a n ( l -2 ) a~M a n 6-phosphate(1-2)a~ManOR), 3 (a~Man(1-2)a~Man 6-phosphate(l+3)a~ManOR), and 4 (a~Man(1-2)a~Man 6-phosphate(l+6)a~ManOR) are being used in a study of the targeting of enzymes to the lysosomes by phosphomannosyl receptors.OM. P. SRIVASTAVA et OLE HINDSGAUL. Can. J. Chem. 64, 2324 (1986). On a rCalisC la synthkse chimique, sous la forme de glycosides mCthoxycarbony1-8 octyles (R = (CH2j8COOCH3), des trois 0-phosphoryl-6 trimannosides (2-4) possibles que l'on retrouve sur les chaines de carbohydrates liCes par l'asparagine dans les enzymes des lysosomes. L'Ctape clC dans la synthkse implique la glycosylation de a-D-mannopyranosides protCgCs d'une fa~on adCquate (5-7) avec le donneur mannobiosyle phosphorylk, le chlorure de 0-(titra-0-acityl-2,3,4,6 a-D-mannopyrannosy1)-2 di-0-benzyl-3,4 0-diphCnylphosphory1-6 a-D-mannopyrannosyle (14), qui conduit i des mClanges des trisaccharides liCs par les positions a et p . On utilise les composCs 2 (aDMan(1-2)a~Man 6-phosphate(l+2)a~ManOR), 3 (a~Man(l+2)aDMan 6-phosphate(l-+3)a~ManOR) et 4 (a~Man(l-2)aDMan 6-phosphate(l+6)a~ManOR) dans une Ctude sur la relation des enzymes avec les lysosomes par le biais des rCcepteurs phosphomannosyles.[Traduit par la revue]

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Properties of a synthetic antigen related to the human blood-group Lewis a

Cited by 310 publications

References 18 publications

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Molecular basis of Escherichia coli colonization of the upper urinary tract in BALB/c mice. Gal-Gal pili immunization prevents Escherichia coli pyelonephritis in the BALB/c mouse model of human pyelonephritis.

Synthesis of the subterminally 6-O-phosphorylated trimannosides found on carbohydrate chains of lysosomal enzymes

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