Microwave-assisted reaction of glycosylamine with aspartic acid

Amino Acids

Volumn 39, Issue 2, 2010, Pages 599-604

  Real Fernández, Feliciana ^a   Nuti, Francesca ^a   Bonache, M Angeles ^a   Boccalini, Marco ^a   Chimichi, Stefano ^a   Chelli, Mario ^a,b   Papini, Anna Maria ^a,c  

^a UNIVERSITY OF FLORENCE   (Italy)

^b ICCOM CNR   (Italy)

^c Université Paris Seine   (France)

Author keywords

Glycosylamino acids; Microwave assisted synthesis; Triazine based coupling reagent

Indexed keywords

AMINOSUGAR; ASPARTIC ACID; FLUORESCAMINE; VANILLIN; AMINE; GLUCOPYRANOSYLAMINE; GLUCOSAMINE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; CROSS COUPLING REACTION; GLYCOSYLATION; HYDROLYSIS; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMISTRY; MICROWAVE RADIATION; RADIATION RESPONSE;

AMINES; ASPARTIC ACID; GLUCOSAMINE; GLYCOSYLATION; MICROWAVES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 84755161448     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-010-0484-8     Document Type: Article

References (24)

1. αFmoc asparagine OPfp esters. J Chem Soc Perkin Trans 1 13:1461-1471
2. Gelens E, Smeets L, Sliedregt L, Van Steen BJ, Kruse CG, Leurs R, Orru RVA (2005) An atom efficient and solvent-free synthesis of structurally diverse amides using microwaves. Tetrahedron Lett 46:3751-3754
3. Kaminski ZJ (1994) The concept of superactive esters. Could peptide synthesis be improved by inventing superactive esters? Int J Pept Protein Res 43:312-319
4. Kaminski ZJ, Papini AM, Kolesinska B, Kolesinska J, Jastrzabek K, Sabatino G, Bianchini R (2005a) Process for the preparation of N-triazinylammonium salts. Applicant: Italvelluti S.p. a. PCT/EP2005/055793
5. Kaminski ZJ, Kolesinska B, Kolesinska J, Sabatino G, Chelli M, Rovero P, Blaszczyk M, Glowka ML, Papini AM (2005b) N-Triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis. J Am Chem Soc 127:16912-16920
6. Kappe CO (2004) Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed 43:6250-6284
7. Kappe CO, Dallinger D (2006) The impact of microwave synthesis on drug discovery. Nat Rev Drug Disc 5:51-63
8. Keglevic D, Valentekovic S (1976) Syntheses and rearrangements of D-glucosyl esters of aspartic acid linked through the 1-or 4-carboxyl group. Carbohydr Res 47:35-48
9. Keglevic D, Valentekovic S, Roglic G, Goles D, Plavsic F (1973) Glycosyl esters of amino acids. Carbohydr Res 29:25-39
10. Keglevic D, Horvat J, Plavsic F (1976) Synthesis and chemical behaviour of D-glycosyl esters of glutamic acid having the side chain carboxyl group involved in the glycosidic linkage. Carbohydr Res 47:49-61
11. Klein J (1958) Preparation of cis-2-hydroxycyclohexaneacetic acid lactone. J Org Chem 23:1209-1210
12. Liautard V, Pillard C, Desvergnes V, Martin OR (2008) One-step synthesis of N-protected glycosylamines from sugar hemiacetals. Carbohydr Res 343:2111-2117
13. Meldal M (1994a) Glycopeptide synthesis. In: Lee YC, Lee RT (eds) Neoglycoconjugates: preparation and application. Academic Press, Orlando, pp 145-198
14. Meldal M (1994b) Recent developments in glycopeptide and oligosaccharide synthesis. Curr Opin Struct Biol 4:710-718
15. Meldal M, Bock K (1994) A general approach to the synthesis of O-and N-linked glycopeptides. Glycoconjugate J 11:59-63
16. Paolini I, Nuti F, Pozo-Carrero MC, Barbetti F, Kolesinska B, Kaminski ZJ, Chelli M, Papini AM (2007) A convenient microwave-assisted synthesis of N-glycosyl amino acids. Tetrahedron Lett 48:2901-2904
17. Rademacher TW, Pareckh RB, Dwek RA (1988) Glycobiology. Ann Rev Biochem 57:785-838
18. Seijas JA, Vazquez-Tato MP, Crecente-Campo J (2007) Microwaveassisted solvent-free synthesis of enol carbamates. Syn Lett 15:2420-2424
19. Soli ED, Manoso MC, Patterson MC, DeShong J (1999) Azide and cyanide displacements via hypervalent silicate intermediates. J Org Chem 64:3171-3177
20. Toshuki I (1994) patent JP 93-77583 19930311
21. Van Ameijde J, Albada HB, Liskamp RJ (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 8:1042-1049
22. Varki A (1999) Essentials of glycobiology, ed. Cold Spring Harbor Laboratory Press, New York
23. Vetter D, Gallop MA (1995) Strategies for the synthesis and screening of glycoconjugates: a library of glycosylamines. Bioconjugate Chem 6:316-318
24. Ying L, Liu R, Zhang J, Lam K, Lebrilla CB, Gervay-Hague J (2005) A topologically segregated one-bead-one-compound combinatorial glycopeptide library for identification of lectin ligands. J Comb Chem 7:372-384