syn- anti- syn- 2- anti Ienega Boc Gold Boc β- HCl Boc R 1 R 2 H R 1 R 2 / R 3 H

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1 櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅 ~ O A Taurine Taurocholate 3 S D -Cysteinolic acid 8 ATAHS GABA 1 Ca S

2 syn- anti- syn- 2- anti Ienega Boc Gold Boc β- HCl Boc R 1 R 2 H R 1 R 2 / R 3 H R 1 R 2 H Boc syn- 2- anti N- 2- Bella

3 Ienega N- Mitsunobu R 1 = H R 2 = R 3 = H N Strecker KCN Mitsunobu R 2 H N-

4 HAYES K C. A review on the biological function of taurine J. Nutrition Rev LIEBOWITZ S M LOMBARDINI J B SALVA P S. Effects of aminocycloalkanesulfonic acid analogs of taurine on ATP-dependent calcium ion uptake and protein 2006 phosphorylation J. Biochem. Pharmac DELLA C L CRICHTON R R DUBURS G et al. The use 29 of taurine analogues to investigate taurine functions and their potential therapeutic applications J. Amino Acids Org. Chem TIMOTHY C BIRDSALL N D. Therapeutic applications of taurine J. Alt. Med. Rev HIGASHIURA K IENAGA K. Simple performic acid oxidation of acetylthio group to sulfonic acid and its applica- 1- tion in syntheses of 2-substituted taurines J. J. Org HAYES K C CAREY R E SCHMIDT S Y. Retinal degeneration associated with taurine deficiency in the cat KSCN J. Science RAIHA N RASSIN D HEINONEN K et al. Milk protein quality and quantity biochemical and growth effects in low birth weight infants LBWI J. Pediatr Res XU J X. Synthesis of hydroxyalkanesulfonic acids aminoalkanesulfonic acids and sulfonopeptides J. Chin. J. Chem RICCI L FROSINI M GAGGELLI N et al. Inhibition of rabbit brain 4-aminobutyrate transaminase by some taurine analogues a kinetic analysis J. Biochem. Pharmacol BRAGHIROLI D TRUZZI C BRANDOLI C et al. Effect of 2-methyltaurine and its enantiomers on arterial blood pressure J. Pharmacol. Res GOLD M H SKEBELSKY M LANG G. The chemistry of aliphatic nitrosulfonates. Ⅱ. β-amino sulfonic acids

5 J. J. Org. Chem Xu C X XU J X. Versatile synthesis of α-substituted taurines from nitroolefins J. Amino Acids CN P HIGASHIURA K MORINA H MATSUURA H et al. Synthesis and properties of optically active 2-substituted taurines J. J. Chem. Soc. Perkin Trans HIGASHIURA K TOYOMAKI Y TENAGA K. The chemical conversion of C-terminal glycines in peptides into taurine J. J. Chem. Soc. Chem. Commun BRAGHIROLI D DI-BELLA M. Asymmetric synthesis of R - and S -2-aminobutanesulfonic Acid and their 3 3-dimethylderivatives J. Tetrahedron Asymmetry BRAGHIROLI D DI-BELLA M. New methods for the preparation of 2-amino-2-methylpropane sulfonic acid J. Tetrahedron Lett ZHANG W WANG B Y CHEN N et al. Expeditious and practical synthesis of various substituted taurines from amino alcohols J. Synthesis HIGASHIURA K IENAGA K. Simple performic acid oxidation of acetythio grooup to sulfonic acid and its application in synthesis of 2-substituted taurines J. J. Org. Chem MOREE W J VAN-DER-MAREL G A LISKAMP R M J. Synthesis of peptidosulfinamides and peptidosulfonamides peptidomimetics containing the sulfinamide or sulfonamide transition-state isostere J. J. Org. Chem WANG B Y ZHANG W ZHANG L L et al. Versatile synthesis of free and N-benzyloxycarbonyl-protected 2 2-disubstituted taurines J. Eur. J. Org. Chem XU J X XU S. Synthesis of N-protected 1-substituted and 2-disubstituted taurines J. Synthesis XU J X XU S ZHANG Q H. The first synthesis of optically active 1-substituted taurines J. Heteroat. Chem CHEN N JIA W Y XU J X. A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines J. Eur. J. Org. Chem XU J X. A new and expeditious asymmetric synthesis of R - and S -2-aminoalkane-sulfonic acids from chiral amino alcohols J. Tetrahedron Asymmetry CHEN N ZHU M ZHANG W et al. Synthesis of gemdisubstituted taurines by thregioselective ring-opening of 2 2-disubstituted aziridines with sodium bisulfite and sulfite J. Amino Acids HU L B ZHU H DU D M et al. Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines J. J. Org. Chem HUANG J X WANG F DU D M et al. An expeditious synthesis of 1-substituted and cyclic taurines J. Synthesis HUANG J X DU D M XU J X. Facile synthesis of 1- disubstituted taurines J. Synthesis YU H CAO S L ZHANG L L et al. Synthesis of α-aliphatic and β-aromatic substituted taurines via the regioselective ammonia ring-opening of thiiranes J. Synthesis Research progress on the synthesis of substituted taurines XU Jia-xi State Key Laboratory of Chemical Resource Engineering and Department of Organic Chemistry Faculty of Science Beijing University of Chemical Technology Beijing China Huaxue Shiji ~ 965 Abstract Taurine and substituted taurines are a class of key naturally occuring amino acids and the sulfur analogs of protein encoded amino acids with important biological activities. The synthetic methods for various substituted taurines including 1- and 2-monosubstituted taurines 1-2- and 2 2- disubstituted taurines especially salt-free methods for convenient preparation highly pure taurines from the author' s research group have been reviewed. Key words taurine substituted taurine amino acid analog synthesis SCI 170 EI

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<4D6963726F736F667420576F7264202D20B9DCC0EDD6C6B6C8BBE3B1E0B5DAB6FEB8E5> 土木工程防灾国家重点实验室 ( 同济大学 ) STATE KEY LABORATORY OF DISASTER REDUCTION IN CIVIL ENGINEERING, TONGJI UNIVERSITY 管理制度汇编土木工程防灾国家重点实验室 ( 同济大学 ) 目录国家重点实验室建设与运行管