Synthesis and NMR studies of cyclopeptides containing a sugar amino acid

被引:45
作者
Stöckle, M [1 ]
Voll, G [1 ]
Günther, R [1 ]
Lohof, E [1 ]
Locardi, E [1 ]
Gruner, S [1 ]
Kessler, H [1 ]
机构
[1] Tech Univ Munich, Inst Organ Chem & Biochem, D-85747 Garching, Germany
关键词
D O I
10.1021/ol026126d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Cyclopeptides containing Glucuronic acid methylamine (Gum) alternating with Gly, L-Ala, D-Ala, L-Phe, D-Phe, L-Lys, or D-Lys were synthesized by a combination of solid-phase synthesis and solution chemistry. A more effective pathway to synthesize the sugar amino acid Gum in higher yields and in a shorter period of time was developed. Gum is employed in the benzylated and deprotected form. The cyclopeptides were characterized by NMR and the structure of one deprotected cyclic peptide solved.
引用
收藏
页码:2501 / 2504
页数:4
相关论文
共 30 条
[1]   Use of onium salt-based coupling reagents in peptide synthesis [J].
Albericio, F ;
Bofill, JM ;
El-Faham, A ;
Kates, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9678-9683
[2]  
*BIOSYM MOL SIM, 1995, DISC VERS 2 98
[3]   RACEMIZATION STUDIES DURING SOLID-PHASE PEPTIDE-SYNTHESIS USING AZABENZOTRIAZOLE-BASED COUPLING REAGENTS [J].
CARPINO, LA ;
EL-FAHAM, A ;
ALBERICIO, F .
TETRAHEDRON LETTERS, 1994, 35 (15) :2279-2282
[4]   ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
[5]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[6]   GEOMETRIC CONSTRAINTS IN 6-MEMBERED AND 8-MEMBERED RINGS [J].
DUNITZ, JD ;
WASER, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (16) :5645-&
[7]   POLYSACCHARIDE ANALOGUES .1. SYNTHESES OF 7-AMINO-2,6-ANHYDRO-7-DEOXY-D-GLYCERO-L-MANNO-HEPTONIC ACID AND 7-AMINO-2,6-ANHYDRO-7-DEOXY-D-GLYCERO-D-GULO-HEPTONIC ACID [J].
FUCHS, EF ;
LEHMANN, J .
CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (07) :2254-2260
[8]  
GRUNER S, 2000, PEPTIDES, P313
[9]  
GRUNER S, UNPUB EUR J CHEM
[10]   Carbohydrate-based mimetics in drug design: Sugar amino acids and carbohydrate scaffolds [J].
Gruner, SAW ;
Locardi, E ;
Lohof, E ;
Kessler, H .
CHEMICAL REVIEWS, 2002, 102 (02) :491-514