Optimized synthesis of aminooxy-peptides as glycoprobe precursors for surface-based sugar-protein interaction studies

被引:24
作者
Jimenez-Castells, Carmen
de la Torre, Beatriz G.
Gallego, Ricardo Gutierrez
Andreu, David
机构
[1] Pompeu Fabra Univ, Dept Expt & Hlth Sci, Barcelona 08003, Spain
[2] Municipal Inst Med Res, Pharmacol Res Unit, Barcelona 08003, Spain
关键词
glycoprobes; surface-based interaction studies; aminooxypeptide; coupling reagent;
D O I
10.1016/j.bmcl.2007.06.090
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An improved procedure for solid phase coupling of Boc-arninooxyacetic acid to peptides is described. By avoiding base-containing activation mixtures which cause over-acylation, it practically suppresses this unwanted side reaction and leads to near quantitative yields of Aoa-peptides, useful as glycoprobe precursors in glycomic studies. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5155 / 5158
页数:4
相关论文
共 27 条
[1]   Inhibition of HIV entry by carbohydrate-binding proteins [J].
Balzarini, J. .
ANTIVIRAL RESEARCH, 2006, 71 (2-3) :237-247
[2]  
Balzarini Jan, 2007, Antiviral Chemistry & Chemotherapy, V18, P1
[3]  
BOND MR, 2007, J CURR OPIN CHEM BIO, V11, P52
[4]  
Brask J, 2000, J PEPT SCI, V6, P290, DOI 10.1002/1099-1387(200006)6:6<290::AID-PSC257>3.0.CO
[5]  
2-L
[6]   TOTAL CHEMICAL SYNTHESIS OF A UNIQUE TRANSCRIPTION FACTOR-RELATED PROTEIN - CMYC-MAX [J].
CANNE, LE ;
FERREDAMARE, AR ;
BURLEY, SK ;
KENT, SBH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :2998-3007
[7]   Controlling the outcome of overacylation of N-protected aminooxyacetic acid during the synthesis of an aminooxy-peptide for chemical ligation [J].
Decostaire, Isidore P. ;
Lelievre, Dominique ;
Zhang, Haihui ;
Delmas, Agnes F. .
TETRAHEDRON LETTERS, 2006, 47 (39) :7057-7060
[8]   Carbohydrate-lectin interactions assessed by surface plasmon resonance [J].
Duverger, E ;
Frison, N ;
Roche, AC ;
Monsigny, M .
BIOCHIMIE, 2003, 85 (1-2) :167-179
[9]  
GAUSEPOHL H, 1989, INT J PEPT PROT RES, V34, P287
[10]   Tailored glycoproteomics and glycan site mapping using saccharide-selective bioorthogonal probes [J].
Hanson, Sarah R. ;
Hsu, Tsui-Ling ;
Weerapana, Eranthie ;
Kishikawa, Kuniyuki ;
Simon, Gabriel M. ;
Cravatt, Benjamin F. ;
Wong, Chi-Huey .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7266-+