D-glucose as a regioselectively addressable scaffold for combinatorial chemistry on solid phase

被引:16
作者
Peri, F
Nicotra, F
Leslie, CP
Micheli, F
Seneci, P
Marchioro, C
机构
[1] Univ Milano Bicocca, Dept Biotechnol & Biosci, I-20126 Milan, Italy
[2] GlaxoSmithKline SpA, Med Res Ctr, Verona, Italy
关键词
combinatorial chemistry; sugars; solid phase; scaffolds;
D O I
10.1081/CAR-120019014
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
D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.
引用
收藏
页码:57 / 71
页数:15
相关论文
共 16 条
[1]   Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence [J].
Danishefsky, SJ ;
Bilodeau, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1380-1419
[2]   Regioselective lipase-catalysed acylation of 4,6-O-benzylidene-α- and -β-D-pyranoside derivatives displaying a range of anomeric substituents [J].
Gridley, JJ ;
Hacking, AJ ;
Osborn, HMI ;
Spackman, DG .
TETRAHEDRON, 1998, 54 (49) :14925-14946
[3]  
Gridley JJ, 1997, SYNLETT, P1397
[4]   Development of an efficient, regio- and stereoselective route to libraries based on the β-D-glucose scaffold [J].
Hirschmann, R ;
Ducry, L ;
Smith, AB .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8307-8316
[5]   NONPEPTIDAL PEPTIDOMIMETICS WITH A BETA-D-GLUCOSE SCAFFOLDING - A PARTIAL SOMATOSTATIN AGONIST BEARING A CLOSE STRUCTURAL RELATIONSHIP TO A POTENT, SELECTIVE SUBSTANCE-P ANTAGONIST [J].
HIRSCHMANN, R ;
NICOLAOU, KC ;
PIETRANICO, S ;
SALVINO, J ;
LEAHY, EM ;
SPRENGELER, PA ;
FURST, G ;
SMITH, AB ;
STRADER, CD ;
CASCIERI, MA ;
CANDELORE, MR ;
DONALDSON, C ;
VALE, W ;
MAECHLER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (23) :9217-9218
[6]  
HISCHMANN R, 1998, J MED CHEM, V41, P1382
[7]  
HISCHMANN R, 1996, J MED CHEM, V39, P2441
[8]   Combinatorial solid-phase synthesis using D-Galactose as a chiral five-dimension-diversity scaffold [J].
Kallus, C ;
Opatz, T ;
Wunberg, T ;
Schmidt, W ;
Henke, S ;
Kunz, H .
TETRAHEDRON LETTERS, 1999, 40 (44) :7783-7786
[9]   Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries [J].
Seeberger, PH ;
Haase, WC .
CHEMICAL REVIEWS, 2000, 100 (12) :4349-+
[10]   Carbohydrate-based small-molecule scaffolds for the construction of universal pharmacophore mapping libraries [J].
Sofia, MJ ;
Hunter, R ;
Chan, TY ;
Vaughan, A ;
Dulina, R ;
Wang, HM ;
Gange, D .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2802-2803