195
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library SynthesisFootnote*

, , , , &
Pages 353-367 | Received 21 Feb 2005, Accepted 04 Apr 2005, Published online: 16 Aug 2006

References

  • Dwek , R. A. 1996 . Glycobiology: Toward understanding the function of sugars . Chem. Rev. , 96 : 683 – 720 .
  • Sears , P. and Wong , C.‐H. 1999 . Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate‐mediated biological recognition . Angew. Chem. Int. Ed. , 38 : 2301 – 2324 .
  • Christensen , M. K. , Meldal , M. , Bock , K. , Cordes , H. , Mouritsen , S. and Elsner , H. 1994 . Synthesis of glycosylated peptide templates containing 6′‐O‐phosphorylated mannose disaccharides and their binding to the cation‐independent mannose 6‐phosphate receptor . J. Chem. Soc. Perkin Trans. 1 , : 1299 – 1310 .
  • Wu , S. H. , Shimazaki , M. , Lin , C. C. , Qiao , L. , Moree , W. J. , Weitz‐Schmidt , G. and Wong , C.‐H. 1996 . Synthesis of fucopeptides as sialyl Lewisx mimetics . Angew. Chem. Int. Ed. , 35 : 88 – 90 .
  • Furka , A. , Sebestyen , F. , Asgedom , M. and Dibo , G. 1991 . General method for rapid synthesis of multicomponent peptide mixtures . Int. J. Pept. Prot. Res. , 37 : 487 – 493 .
  • Lam , K. S. , Salmon , S. E. , Hersh , E. M. , Hruby , V. J. , Kazmierski , W. M. and Knapp , R. J. 1991 . A new type of synthetic peptide library for identifying ligand‐binding activity . Nature , 354 : 82 – 84 .
  • St Hilaire , P. M. , Lowary , T. L. , Meldal , M. and Bock , K. 1998 . Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries . J. Am. Chem. Soc. , 120 : 13312 – 13320 .
  • Youngquist , R. S. , Fuentes , G. R. , Lacey , M. P. and Keough , T. 1995 . Generation and screening of combinatorial peptide libraries designed for rapid sequencing by mass spectrometry . J. Am. Chem. Soc. , 117 : 3900 – 3906 .
  • Gerz , M. , Matter , H. and Kessler , H. 1993 . S‐glycosylated cyclic peptides . Angew. Chem. Int. Ed. , 32 : 269 – 271 .
  • Salvador , L. A. , Elofsson , M. and Kihlberg , J. 1995 . Preparation of building blocks for glycopeptide synthesis by glycosylation of Fmoc amino acids having unprotected carboxyl groups . Tetrahedron , 51 : 5643 – 5656 .
  • Nicolaou , K. C. , Chucholowski , A. , Dolle , R. E. and Randall , J. L. 1984 . Reactions of glycosyl fluorides. Synthesis of O‐, S‐, and N‐glycosides . J. Chem. Soc. Chem. Commun. , : 1155 – 1156 .
  • Käsbeck , L. and Kessler , H. 1997 . Synthesis of S‐α‐D‐glucosylated L‐cysteine—a novel S‐glycosyl amino acid . Liebigs Ann./Recueil , : 165 – 167 .
  • Monsigny , M. L.P. , Delay , D. and Vaculik , M. 1977 . Synthesis of a new type of glycoconjugate. L‐Cysteine thio‐β‐D‐glycopyranoside . Carbohydr. Res. , 59 : 589 – 593 .
  • Jobron , L. and Hummel , G. 2000 . Solid‐phase synthesis of new S‐glycoamino acid building blocks . Org. Lett. , 2 : 2265 – 2267 .
  • Meldal , M. and Bock , K. 1990 . Pentafluorophenyl esters for temporary carboxyl group protection in solid phase synthesis of N‐linked glycopeptides . Tetrahedron Lett. , 31 : 6987 – 6990 .
  • van Ameijde , J. , Albada , H. B. and Liskamp , R. M.J. 2002 . A convenient preparation of several N‐linked glycoamino acid building blocks for efficient solid‐phase synthesis of glycopeptides . J. Chem. Soc. Perkin Trans. 1 , : 1042 – 1049 .
  • Meinjohanns , E. , Meldal , M. , Paulsen , H. , Dwek , R. A. and Bock , K. 1998 . Novel sequential solid‐phase synthesis of N‐linked glycopeptides from natural sources . J. Chem. Soc. Perkin Trans. 1 , : 549 – 560 .
  • Urge , L. , Otvos , L. , Lang , E. , Wroblewski , K. , Laczko , I. and Hollosi , M. 1992 . Fmoc‐protected, glycosylated asparagines potentially useful as reagents in the solid‐phase synthesis of N‐glycopeptides . Carbohydr. Res. , 235 : 83 – 93 .
  • Mizuno , M. , Muramoto , I. , Kobayashi , K. , Yaginuma , H. and Inazu , T. 1999 . A simple method for the synthesis of N β‐glycosylated‐asparagine and ‐glutamine derivatives . Synthesis , : 162 – 165 .
  • Christiansen‐Brams , I. , Meldal , M. and Bock , K. 1993 . Protected‐mode synthesis of N‐linked glycopeptides: single‐step preparation of building blocks as peracetyl glycosylated N αFmoc asparagine OPfp esters . J. Chem. Soc. Perkin Trans. 1 , : 1461 – 1471 .
  • Taylor , C. M. 1998 . Glycopeptides and glycoproteins: focus on the glycosidic linkage . Tetrahedron , 54 : 11317 – 11362 .
  • Khorlin , A. Y. , Zurabyan , S. E. and Macharadze , R. G. 1980 . Synthesis of glycosylamides and 4‐N‐glycosyl‐L‐asparagine derivatives . Carbohydr. Res. , 85 : 201 – 208 .
  • Gunther , W. and Kunz , H. 1990 . Synthesis of a β‐mannosyl‐chitobiosyl‐asparagine conjugate—a central core region unit of the N‐glycoproteins . Angew. Chem. Int. Ed. , 29 : 1050 – 1051 .
  • Ratcliffe , A. J. , Konradsson , P. and Fraser‐Reid , B. 1990 . n‐Pentenyl glycosides as efficient synthons for promoter‐mediated assembly of N‐α‐linked glycoproteins . J. Am. Chem. Soc. , 112 : 5665 – 5667 .
  • Sasaki , M. , Tachibana , K. and Nakanishi , H. 1991 . An efficient and stereocontrolled synthesis of the nephritogenoside core structure . Tetrahedron Lett. , 32 : 6873 – 6876 .
  • Green , M. and Berman , J. 1990 . Preparation of pentafluorophenyl esters of Fmoc protected amino acids with pentafluorophenyl trifluoroacetate . Tetrahedron Lett. , 31 : 5851 – 5852 .
  • Likhosherstov , L. M. , Novikova , O. S. , Derevitskaja , V. A. and Kochetkov , N. K. 1986 . A new simple synthesis of amino sugar β‐D‐glycosylamines . Carbohydr. Res. , 146 : c1 – c5 .
  • Bodanszky , M. and Martinez , J. 1978 . Side reactions in peptide synthesis. 8. On the phenacylgroup in the protection of the β‐carboxyl function of aspartyl residues . J. Org. Chem. , 43 : 3071 – 3073 .
  • Anisfeld , S. T. and Lansbury , P. T. 1990 . A convergent approach to the chemical synthesis of asparagine‐linked glycopeptides . J. Org. Chem. , 55 : 5560 – 5562 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.