A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis

被引:25
作者
Nakamura, K
Ishii, A
Ito, Y
Nakahara, Y
机构
[1] Tokai Univ, Dept Ind Chem, Hiratsuka, Kanagawa 2591292, Japan
[2] Inst Phys & Chem Res, RIKEN, Wako, Saitama 3510198, Japan
关键词
glycopeptides; solid-phase synthesis; silicon halides;
D O I
10.1016/S0040-4020(99)00649-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:11253 / 11266
页数:14
相关论文
共 23 条
[1]  
[Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881
[2]   Development of a novel silyl ether linker for solid-phase organic synthesis [J].
Boehm, TL ;
Showalter, HDH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6498-6499
[3]  
CHENERA B, 1995, J AM CHEM SOC, V117, P11999
[4]   Organic chemistry on solid supports [J].
Fruchtel, JS ;
Jung, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42
[5]   Solid-phase organic reactions: A review of the recent literature [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, D .
TETRAHEDRON, 1996, 52 (13) :4527-4554
[6]   Ester enolate Claisen rearrangement using a polymer-supported silyl triflate [J].
Hu, Y ;
Porco, JA .
TETRAHEDRON LETTERS, 1999, 40 (17) :3289-3292
[7]   Alcoholysis and carbonyl hydrosilylation reactions using a polymer-supported trialkylsilane [J].
Hu, YH ;
Porco, JA .
TETRAHEDRON LETTERS, 1998, 39 (18) :2711-2714
[8]   Novel polymer-supported trialkylsilanes and their use in solid-phase organic synthesis [J].
Hu, YH ;
Porco, JA ;
Labadie, JW ;
Gooding, OW ;
Trost, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4518-4521
[9]  
ISHIHARA T, 1991, Patent No. 374676
[10]   A NEW FLUORIDOLYZABLE ANCHORING LINKAGE FOR ORTHOGONAL SOLID-PHASE PEPTIDE-SYNTHESIS - DESIGN, PREPARATION, AND APPLICATION OF THE N-(3 OR 4)-[[4-(HYDROXYMETHYL)PHENOXY]-TERT-BUTYLPHENYLSILYL]PHENYL PENTANEDIOIC ACID MONOAMIDE (PBS) HANDLE [J].
MULLEN, DG ;
BARANY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22) :5240-5248