Expedient synthesis of triazole-linked glycosyl amino acids and peptides

被引:196
作者
Kuijpers, BHM
Groothuys, S
Keereweer, AR
Quaedflieg, PJLM
Blaauw, RH
van Delft, FL
Rutjes, FPJT
机构
[1] Univ Nijmegen, NSRIM, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands
[2] DSM Res & Patents, Life Sci Adv Synth, Catal & Dev, NL-6160 MD Geleen, Netherlands
[3] Chiralix BV, NL-6525 EC Nijmegen, Netherlands
关键词
D O I
10.1021/ol048841o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expedient, high-yielding synthesis of two types of triazole-linked glycopeptides is described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3 + 2] cycloaddition of either azide-functionalized glycosides and acetylenic amino acids or acetylenic glycosides and azide-containing amino acids.
引用
收藏
页码:3123 / 3126
页数:4
相关论文
共 39 条
[1]   Synthesis of 1′-β-D-glucopyranosyl-1,2,3-triazole-4,5-dimethanol-4,5-bis-(isopropylcarbamate) as potential antineoplastic agent [J].
Al-Masoudi, NA ;
Al-Soud, YA .
TETRAHEDRON LETTERS, 2002, 43 (22) :4021-4022
[2]   Metal catalyzed diazo transfer for the synthesis of azides from amines [J].
Alper, PB ;
Hung, SC ;
Wong, CH .
TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032
[3]   1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].
ALVAREZ, R ;
VELAZQUEZ, S ;
SANFELIX, A ;
AQUARO, S ;
DECLERCQ, E ;
PERNO, CF ;
KARLSSON, A ;
BALZARINI, J ;
CAMARASA, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194
[4]   A NEW METHOD OF ANOMERIC PROTECTION AND ACTIVATION BASED ON THE CONVERSION OF GLYCOSYL AZIDES INTO GLYCOSYL FLUORIDES [J].
BRODER, W ;
KUNZ, H .
CARBOHYDRATE RESEARCH, 1993, 249 (01) :221-241
[5]   UNUSUAL REACTIVITY OF 4-CARBOXYAMIDO-2-OXAZOLINE SYSTEMS - NEW SYNTHESIS OF OPTICALLY-ACTIVE N-SULFONYL DERIVATIVES [J].
COSSU, S ;
GIACOMELLI, G ;
CONTI, S ;
FALORNI, M .
TETRAHEDRON, 1994, 50 (17) :5083-5090
[6]   Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling [J].
Dondoni, A ;
Mariotti, G ;
Marra, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4475-4486
[7]  
Dondoni A, 2001, SYNTHESIS-STUTTGART, P2129
[8]   A concise C-glycosyl amino acid synthesis by alkenyl C-glycoside-vinyloxazolidine cross-metathesis.: Synthesis of glycosyl serine, asparagine and hydroxynorvaline isosteres [J].
Dondoni, A ;
Giovannini, PP ;
Marra, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (19) :2380-2388
[9]   Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides [J].
Dondoni, A ;
Marra, A .
CHEMICAL REVIEWS, 2000, 100 (12) :4395-+
[10]   Recent advances in stereoselective C-glycoside synthesis [J].
Du, YG ;
Linhardt, RJ ;
Vlahov, IR .
TETRAHEDRON, 1998, 54 (34) :9913-9959