New prototypical O-linked-glycopeptidomimetics corresponding to the linkage region of proteoglycans

被引:23
作者
Kim, JM [1 ]
Roy, R [1 ]
机构
[1] UNIV OTTAWA,DEPT CHEM,OTTAWA,ON K1N 6N5,CANADA
关键词
D-xylose; oligoglycine; peptoid; peptidomimetic; proteoglycan;
D O I
10.1016/S0008-6215(96)00301-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new class of glycopeptidomimetic composed of N-substituted oligoglycine (peptoid) mimicking the beta-D-Xyl-(1 --> 3)-O-L-Ser linkage region of proteoglycans was synthesized using a convergent approach. Reiterative N-alkylation-N-bromoacetylation reactions were used starting from tert-butyl bromoacetate (1) and isopropylamine. Perbenzoylated 2-aminoethyl beta-D-xylopyranoside 10 constituted the key glycan L-Ser mimic. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:173 / 179
页数:7
相关论文
共 17 条
[1]   SYNTHESIS OF GLYCURONAMIDES OF AMINO-ACIDS, CONSTITUENTS OF MICROBIAL POLYSACCHARIDES AND THEIR CONVERSION INTO NEOGLYCOCONJUGATES OF COPOLYMER TYPE [J].
CHERNYAK, AY ;
SHARMA, GVM ;
KONONOV, LO ;
KRISHNA, PR ;
RAO, AVR ;
KOCHETKOV, NK .
GLYCOCONJUGATE JOURNAL, 1991, 8 (02) :82-89
[2]   SYNTHESIS OF 1,2-TRANS-RELATED 1-THIOGLYCOSIDE ESTERS [J].
FERRIER, RJ ;
FURNEAUX, RH .
CARBOHYDRATE RESEARCH, 1976, 52 (DEC) :63-68
[3]   STRUCTURE OF COLLAGEN FIBRIL-ASSOCIATED, SMALL PROTEOGLYCANS OF MAMMALIAN ORIGIN [J].
GARG, HG ;
LYON, NB .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1991, 49 :239-261
[4]   PEPTOIDS - A NEW APPROACH TO THE DEVELOPMENT OF PHARMACEUTICALS [J].
KESSLER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04) :543-544
[5]  
KIMM JM, 1996, CARBOHYDR LETT, V1, P465
[6]  
KJELLEN L, 1991, ANNU REV BIOCHEM, V60, P443, DOI 10.1146/annurev.bi.60.070191.002303
[7]  
KRUIJTZER JAW, 1995, TETRAHEDRON LETT, V36, P6969, DOI 10.1016/0040-4039(95)01382-R
[8]  
ROY R, 1996, J CHEM SOC CHEM COMM, P201
[9]  
ROY R, IN PRESS ACS S SER
[10]  
ROY R, 1997, IN PRESS HDB PHASE T