Recent carbohydrate-based chemoselective ligation applications

被引:68
作者
Langenhan, JM [1 ]
Thorson, JS [1 ]
机构
[1] Univ Wisconsin, Sch Pharm, Lab Biosynthet Chem, Madison, WI 53705 USA
关键词
D O I
10.2174/1570179052996937
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chemoselective ligation reactions are highly efficient and specific covalent bond forming reactions capable of proceeding within a physiological environment. Chemoselective ligations offer exquisite specificity, similar to enzymatic reactions, but with the significant advantage of accessing a Much broader range of coupling partners. Thus, even among a multitude of reactive functional groups, two ligation partners exclusively react with one another. While chemoselective ligation has been used in many applications, the focus of this review is the application of chemoselective ligation reactions toward carbohydrate-based structures. More specifically, recent applications are presented in areas such as immobilized carbohydrate arrays, cell-surface engineering, glycoproteins/peptides, and glycosylated natural products.
引用
收藏
页码:59 / 81
页数:23
相关论文
共 228 条
[91]   Total chemical synthesis of a 27 kDa TASP protein derived from the MscL ion channel of M-tuberculosis by ketoxime-forming ligation [J].
Kochendoerfer, GG ;
Tack, JM ;
Cressman, S .
BIOCONJUGATE CHEMISTRY, 2002, 13 (03) :474-480
[92]   Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies [J].
Koeller, KM ;
Wong, CH .
CHEMICAL REVIEWS, 2000, 100 (12) :4465-4493
[93]   Staudinger ligation:: A new immobilization strategy for the preparation of small-molecule arrays [J].
Köhn, M ;
Wacker, R ;
Peters, C ;
Schröder, H ;
Soulère, L ;
Breinbauer, R ;
Niemeyer, CM ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (47) :5830-5834
[94]  
Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO
[95]  
2-X
[96]   MODIFICATION OF CELL-SURFACES BY ENZYMATIC INTRODUCTION OF SPECIAL SIALIC-ACID ANALOGS [J].
KOSA, RE ;
GROSS, HJ .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1993, 190 (03) :914-920
[97]   Glycosides in medicine:: "The role of glycosidic residue in biological activity" [J].
Kren, V ;
Martínková, L .
CURRENT MEDICINAL CHEMISTRY, 2001, 8 (11) :1303-1328
[98]  
Lang I, 1998, J PEPT SCI, V4, P72, DOI 10.1002/(SICI)1099-1387(199802)4:1<72::AID-PSC130>3.0.CO
[99]  
2-G
[100]  
LANGENHAN JM, UNPUB