An Alternative Access to a Trisaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Serotype 19A

スポンサーリンク

概要

• 論文の詳細を見る

• A chemical synthesis has been achieved for β-D-ManNAc-(1→4)-α-D-Glc-(1→3)-L-Rha, a trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae serotype 19A, by stepwise link-up of the suitably functionalized, constituent sugar units. A β-selective glycosylation of trimethylsilylethyl glucoside having free 4-OH with 2-(benzoyloxyimino)-2-deoxyglycosyl bromide, followed by manno-selective hydroboration, N-acetylation, and functionalization of the anomeric center (1-OSE→1-OH→1-F), gave a key disaccharide donor, β-D-ManNAc-(1→4)-α-D-Glc-(1→F. Ensuing glycosylation of an L-rhamnosyl acceptor with the donor substrate afforded, after deblocking, the target trisaccharide in 6.5% yield over 13 steps from D-glucose.

• 公益社団法人日本薬学会の論文
• 1996-02-15

著者

• Takayanagi Hiroaki

  School Of Pharmaceutical Sciences Kitasato University

• KAJI Eisuke

  School of Pharmaceutical Sciences, Kitasato University

• OSA Yumiko

  School of Pharmaceutical Sciences, Kitasato University

• Osa Yumiko

  School Of Pharmaceutical Sciences Kitasato University

• Kaji Eisuke

  School Of Pharmaceutical Sciences Kitasato University

• Takada A

  Waseda Univ. Tokyo Jpn

• TANAIKE Mutsumi

  School of Pharmaceutical Sciences, Kitasato University

• HOSOKAWA Yugo

  School of Pharmaceutical Sciences, Kitasato University

• TAKADA Atsushi

  School of Pharmaceutical Sciences, Kitasato University

• Hosokawa Yugo

  Yakult Central Institute For Microbiological Research

• Tanaike Mutsumi

  School Of Pharmaceutical Sciences Kitasato University

• HOSOKAWA Yukiko

  Yakult Central Institute for Microbiological Research

• Takada Atsushi

  School Of Pharmaceutical Sciences Kitasato University

• Takayanagi Hiroaki

  School of Parmaceutical Sciences, Kitasato University

関連論文

• Studies on Sialic Acids. VIII. : The 1,4-Lactone Derivatives of N-Acetylneuraminic Acid(Organic,Chemical)
• Catalytic Aerobic Oxidation of nor-Binaltorphimine (nor-BNI) Analogs without 4, 5-Epoxy Bridge Affords a More Selective Ligand for κ Opioid Receptor than the Representative κ Antagonist nor-BNI
• Crystal Structure of 1,2-Bis(N-methy1-2-fluorobenzoylamino)benzene
• Crystal Structure of 2, 8, 14-Trimethyl-2, 8, 14-triazatetracyclo-[14^, 7, 2^]tetracosa-4, 6, 10, 12, 16, 18, 19, 21, 23-nonaene^3, 9, 15-trione
• Synthesis of a New Phenol Glycoside, Neohancoside C from Cynanchum hancockianum
• Crystal Structure of N-(3S,3aS,5aS,8S,9R,9aR,9bS)-3a,4,5,5a,6,7,8,9,9a,9b-Decahydro-8-[2(2,6-dioxanyl)ethoxy]-3,5a-9trimethyl-2(3H)-naphtho[1,2-b]-furanone(1)and (3S,3aS,5aS,8S,9R,9aR,9bS)-3a,4,5,5a,6,7,8,9,9a,9b-Decahydro-8-[2(2,6-dioxanyl)ethoxy]-3,5a-9
• Studies on Picrates. IX. Crystal Structures of o-Xylene and p-Xylene Picrates
• Conformation of the Cyclohexenone Ring of 1α-Chloro-2β-bromo-1, 2-dihydro-6β-santonin
• Conformational Analysis of Methyl 2,3,4-Tri-O-acetyl-6-deoxy-6-phenylsulfinyl-α-D-glucoside
• 1 : 1 Molecular Complex of α-Santonin and Nitric Acid
• Studies on Picrate. VIII. Crystal and Molecular Structures of Aromatic Amine Picrates : Aniline, N-Methylaniline, N, N-Dimethylaniline and o-, m- and p-Phenylenediamine Picrates
• A Novel Glycosylation of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) via in Situ Pyranose-Furanose Rearrangement
• Reaction Products from Fischer's Methylation of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN)
• Synthesis and Inhibitory Activities of Isochromophilone Analogues against gp120-CD4 Binding
• Synthesis and Utility of 2-(Benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl Bromide as a Novel α-D-Talosaminide Building Block
• A Practical Synthesis of Mannosaminyl-β(1→4)-glucosyl-α(1→2)-rhamnose, the Trisaccharide Repeating Unit of a Streptococcus pneumoniae Capsular Polysaccharide
• Synthesis of a 2-Acetamido-2-deoxy-β-D-mannuronic Acid-Containing Artificial Glycolipid Corresponding to the Repeating Unit of Teichuronic Acid from Micrococcus luteus
• A Pracitical, Highly Stereoselective Synthesis of the Trisaccharide Repeating Unit of a Streptococcus pneumoniae Polysaccharide
• Crystal Structure of N-(10,11-Digydro-5H-dibenzo[a,d]cycloheptan-5-yl)-piperazine Hydrochloride
• Expedient Synthesis of an Anomerically Modified Trisaccharide Component of the Capsular Polysaccharide from Streptococcus pneumoniae Type 19F
• An Alternative Access to a Trisaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Serotype 19A
• Antimicrobial C-Glucoside from Aerial Parts of Diospyros nigra
• Synthesis of cis- and trans-5, 8-Dihydroxy-5, 6, 7, 8-tetrahydro-1, 4-naphthoquinone
• P-325 A Ring-Opening Reaction Of N-Cyclopropylmethyl Group In Naltrexone By Use Of PtO_2
• A Novel, Readily Accessible Lactosaminyl Donor : N-Trichloroethoxycarbonyl-hexa-0-benzoyl-β-D-lactosaminyl Fluoride :
• P-322 Oxidations of Morphinan Derivatives with Pyrrole Ring
• Plasma Pharmacokinetics of 7-Ethyl-10-hydroxycamptothecin (SN-38) after Intravenous Administration of SN-38 and Irinotecan (CPT-11) to Rats
• Simultaneous Determination of the Lactone and Carboxylate Forms of 7-Ethyl-10-hydroxycamptothecin (SN-38), the Active Metabolite of Irinotecan (CPT-11), in Rat Plasma by High Performance Liquid Chromatography
• Syntheses and Mass Spectrometric Analysis of Amidinothiourea Derivatives
• PA83 STUDIES ON 3-DEOXY-D__=-GLYCERO-D__=-GALACTO-2-NONULOPYRANOSONIC ACID (KDN)
• Crystal Structure of Methyl(8R, 11R, 14S)-8-[N-[(tert-Butoxy)carbonyl]amino]-11-(3, 5-dichloro-4-hydroxyphenyl)-18, 19-dibromo-5-iodo-4-hydroxy-13-methyl-9, 12-dioxo-10, 13-diaza-2-oxatricyclo[14. 2. 2. 1^]heneicosa-3, 5, 7(21), 16, 18, 19-hexaene-1
• Photochemical Production of Sugar-like Interconvertible Anomeric Naphthopyranylhemiacetals from Acenaphthylene and Chloranil
• The crystal structure of (4R,7S)-7-isopropyl-4-methyl-2-azepanone ((-)-menthone lactam).
• Studies on the chlorinated .ALPHA.-santonins. III. Revised structure of .ALPHA.-santonin chlorohydrin.
• The crystal structure of phenanthrene:Picric acid molecular complex.
• The crystal structure of calcium sulfite tetrahydrate. Interatomic distances and angles.
• Molecular structure of 3,4,6-tri-O-acetyl-1,2-O-((1S)-1-(2-p-bromophenyl)-9H-imidazo(1,2-a)benzimidazol-3-yl)ethylidene)-.ALPHA.-D-glucopyranose acetone solvate.
• Studies on lactams. VII. Conformation of D-glucono-1,5-lactam.
• Studies on 5-8 fused ring compounds. III. Hydrogenolysis of 4,4-dimethyltricyclo[6.3.0.01,7]undecane-2,6-dione.
• A facile synthesis of anomeric methyl DL-tolyposaminides, methyl DL-forosaminides, and related substances.

もっと見る 閉じる

スポンサーリンク