Preparation of Some Glycosyl Amino Acid Building Blocks via Click Reaction and Construction of a Glycotetrapeptide Library Using Spot Synthesis

REFERENCES

• Sharon , N. and Lis , H. 1989 . Lectins as cell recognition molecules . Science , 246 : 227 – 234 .
   PubMed Web of Science ®Google Scholar
• Seitz , O. 2000 . Glycopeptide synthesis and the effects of glycosylation on protein structure and activity . ChemBioChem , 1 : 214 – 246 .
   Google Scholar
• Sampson , N. S. , Mrksich , M. and Bertozzi , R. C. 2001 . Surface molecular recognition . Proc. Natl. Acad. Sci. USA , 98 : 12870 – 12871 .
   Google Scholar
• Rudd , P. M. , Elliott , T. , Cresswell , P. , Wilson , I. A. and Dwek , R. A. 2001 . Glycosylation and the immune system . Science , 291 : 2370 – 2376 .
   PubMed Web of Science ®Google Scholar
• Crocker , P. R. 2001 . Mammalian Carbohydrate Recognition Systems , 1 – 249 . Heidelberg : Springer .
   Google Scholar
• Danishefsky , J. S. and Allen , J. R. 2000 . From the laboratory to the clinic: a retrospective on fully synthetic carbohydrate-based anticancer vaccines . Angew. Chem. Int. Ed. Engl. , 39 : 836 – 863 .
   PubMed Web of Science ®Google Scholar
• Ziegler , T. , Röseling , D. and Subramanian , L. R. 2002 . Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates . Tetrahedron: Asymm. , 13 : 911 – 914 .
   Web of Science ®Google Scholar
• Schips , C. and Ziegler , T. 2005 . A practical one-pot synthesis of new S-glycosyl amino acid building blocks for combinatorial neoglycopeptide synthesis . J. Carbohydr. Chem. , 24 : 773 – 788 .
   Web of Science ®Google Scholar
• Ziegler , T. and Schips , C. A process for the Mitsunobu coupling of 1-thiohexoses and aminoaclohols . Ger. Patent, DE 102004046010 . 2005 . Chem. Abstr. 2005, 144, 36465
   Google Scholar
• Ziegler , T. and Schips , C. 2006 . An efficient Mitsunobu protocol for the one-pot synthesis of S-glycosyl amino acid building blocks and their use in combinatorial spot synthesis of glycopeptide libraries . Nature Protocols , 1 : 1987 – 1994 .
   Google Scholar
• Huisgen , R. , Knorr , R. , Möbius , L. and Szeimies , G. 1965 . Einige Beobachtungen zur Addition organischer Azide an CC-Dreifachbindungen . Ber. Dtsch. Chem. Ges. , 98 : 4014 – 4021 .
   Google Scholar
• Sharpless , K. B. , Fokin , V. V. , Green , L. G. and Rostovtsev , V. V. 2002 . A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes . Angew. Chem. Int. Ed. , 41 : 2596 – 2599 .
   PubMed Web of Science ®Google Scholar
• Meldal , M. , Christensen , C. and Tornoe , C. W. 2002 . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides . J. Org. Chem. , 67 : 3057 – 3064 .
   Google Scholar
• Bock , V. D. , Hiemstra , H. and van Maarseveen , J. H. 2006 . Cu(I)-catalyzed alkyne-azide “Click” cycloadditions from mechanism and synthetic perspective . Eur. J. Org. Chem. , : 51 – 68 .
   Google Scholar
• Pietrzik , N. , Schips , C. and Ziegler , T. 2008 . Efficient synthesis of glycosylated asparaginic acid building blocks via click chemistry . Synthesis , : 519 – 526 .
   Google Scholar
• Dedola , S. , Nepogodiev , S. A. and Field , R. A. 2007 . Recent applications of the Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry . Org. Biomol. Chem. , 5 : 1006 – 1017 .
   PubMed Web of Science ®Google Scholar
• Winkinson , B. L. , Bornaghi , L. F. , Poulson , A.-A. and Houston , T. A. 2006 . Synthetic utility of glycosyl triazoles in carbohydrate chemistry . Tetrahedron , 62 : 8115 – 8125 .
   Google Scholar
• Fernandez-Megia , E. , Correa , J. , Rodriguez-Meizoso , I. and Riguera , R. 2006 . A click approach to unprotected glycodendtrimers . Macromol. , 39 : 2113 – 2120 .
   Web of Science ®Google Scholar
• Perion , R. , Ferrieres , V. , Garcia-Moreno , M. I. , Mellet , C. O. , Duval , R. , Fernandez , J. M. G. and Plusquellec , D. 2005 . 1,2,3-Triazoles and related glycoconjugates as new glycosidase inhibitors . Tetrahedron , 61 : 9118 – 9128 .
   Google Scholar
• Bodine , K. D. , Gin , D. Y. and Gin , M. S. 2005 . Highly convergent synthesis of C3- or C2-symmetrical carbohydrate macrocycles . Org. Lett. , 7 : 4479 – 4482 .
   Google Scholar
• Dörner , S. and Westermann , B. 2005 . A short route for the synthesis of sweet macrocycles via a click-dimerization-ring-closing metathesis approach . Chem. Commun. , : 2852 – 2854 .
   Google Scholar
• Hoffmann , B. , Bernet , B. and Vasella , A. 2002 . Oligosaccharide analogues of polysaccharides. Part 24. Synthesis of cyclodextrin analogues containing a substituted buta-1,3-diyne or a 1,2,3-triazole unit and analysis of intramolecular hydrogen bonds . Helv. Chim. Acta , 85 : 265 – 287 .
   Google Scholar
• Dos Anjos , J. V. , Sinou , D. , de Melo , S. J. and Srivastava , R. M. 2007 . Synthesis of triazole-linked manno- and glucopyranosyl amino acids . Synthesis , : 2647 – 2652 .
   Google Scholar
• Angell , Y. L. and Burgess , K. 2007 . Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions . Chem. Soc. Rev. , 36 : 1674 – 1689 .
   PubMed Web of Science ®Google Scholar
• Jiang , J. , Biggins , J. B. and Thorson , J. S. 2001 . Expanding the pyrimidine diphosphosugar repertoire: the chemoenzymatic synthesis of amino- and acetamidoglucopyranosyl derivatives . Angew. Chem. Int. Ed. Engl. , 40 : 1502 – 1505 .
   Google Scholar
• Maunier , V. , Boullanger , P. , Lafont , D. and Chevalier , Y. 1997 . Synthesis and surface-active properties of amphiphilic 6-aminocarbonyl derivatives of D-glucose . Carbohydr. Res. , 299 : 49 – 57 .
   Web of Science ®Google Scholar
• Joosten , J. A. F. , Evers , B. , van Summeren , R. P. , Kamerling , J. P. and Vliegenthart , J. F. G. 2003 . Synthesis of β -D-Galp-(1-4)-β -D-GlcpNAc-(1-2)-α -D-Manp-(1-O)(CH2)7CH3 mimics to explore the substrate specificity of sialyltransferases and trans-sialidases . Eur. J. Org. Chem. , : 3569 – 3586 .
   Google Scholar
• Cottaz , S. , Brimacombe , J. S. and Ferguson , M. A. J. 1993 . An imino-linked carba-disaccharide α -D-mannosidase inhibitor . Carbohydr. Res. , 247 : 341 – 345 .
   Google Scholar
• Billing , J. F. and Nilsson , U. J. 2005 . Cyclic peptides containing a δ -sugar amino acid—synthesis and evaluation as artificial receptors . Tetrahedron , 61 : 863 – 874 .
   Google Scholar
• Yan , R.-B. , Yang , F. , Wu , Y. , Zhang , L.-H. and Ye , X.-S. 2005 . An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransfer reaction . Tetrahedron Lett. , 46 : 8993 – 8995 .
   Web of Science ®Google Scholar
• Bai , Y. , Boons , G. J. , Burton , A. , Johnson , M. and Haller , M. 2000 . Vinyl glycosides in oligosaccharide synthesis (part 6): 3-buten-2-YL 2-azido-2-deoxy glycosides and 3-buten-2-YL 2-phthalimido-2-deoxy glycosides as novel glycosyl donors . J. Carbohydr. Chem. , 19 : 939 – 958 .
   Web of Science ®Google Scholar
• Perez-Balderas , F. , Ortega-Munoz , M. , Morales-Sanfrutos , J. , Hernandez-Mateo , F. , Calvo-Flores , F. G. , Calvo-Asin , J. A. , Isac-Garcia , J. and Santoyo-Gonzales , F. 2003 . Multivalent neoglycoconjugates by regiospecific cycloaddition of alkynes and azides using organic soluble copper catalysts . Org. Lett. , 5 : 1951 – 1954 .
   PubMed Web of Science ®Google Scholar
• Frank , R. 1992 . Spot-synthesis: an easy technique for the positionally addressable, parallel chemical synthesis on a membrane support . Tetrahedron , 48 : 9217 – 9232 .
   Web of Science ®Google Scholar
• Frank , R. 2002 . The SPOT-synthesis technique: synthetic peptide arrays on membrane supports—principles and applications . J. Immunol. Meth. , 267 : 13 – 26 .
   PubMed Web of Science ®Google Scholar
• Ast , T. , Heine , N. , Germeroth , L. , Schneider-Mergener , J. and Wenschuh , H. 1999 . Efficient assembly of peptomers on continuous surfaces . Tetrahedron Lett. , 40 : 4317 – 4318 .
   Web of Science ®Google Scholar
• Ast , T. , Heine , N. , Germeroth , L. , Schneider-Mergener , J. and Wenschuh , H. 2003 . Synthesis and screening of peptoid arrays on cellulose membranes . Tetrahedron , 59 : 9919 – 9930 .
   Google Scholar
• Czarnik , A. W. 2001 . Solid-Phase Organic Synthesis . John Wiley & Sons, USA , 1 : 17
   Google Scholar
• Koretz , K. , Leman , J. , Brandt , I. and Möller , P. 1987 . Metachromasia of 3-amino-9-ethylcarbazole (AEC) and its prevention in immunoperoxidase techniques . Histochem. , 86 : 471 – 478 .
   Google Scholar
• Frey , A. , Meckelein , B. , Externest , D. and Schmidt , M. A. 2000 . A stable and highly sensitive 3,3X,5,5X-tetramethylbenzidine-based substrate reagent for enzyme-linked immunosorbent assays . J. Immunol. Meth. , 233 : 47 – 56 .
   PubMed Web of Science ®Google Scholar
• Poor , M. L. , Santa , P. F. and Sittampalam , G. S. 1988 . Visualization of multiple protein bands on the same nitrocellulose membrane by double immunoblotting . Analytical Biochem. , 175 : 191 – 195 .
   Google Scholar
• Kobayashi , R. and Tashima , Y. 1989 . Visualization of antigen on nitrocellulose membrane by the oxidative coupling reaction of A/,N′-dimethyl-p-phenylendiamine and 4-chloro-1–naphthol . Anal. Biochem. , 183 : 9 – 12 .
   PubMedGoogle Scholar