Synthesis of tyrocidine A and its analogues by spontaneous cyclization in aqueous solution

被引：42
作者：
Bu, XZ
Wu, XM
Xie, GY
Guo, ZH [1 ]
机构：
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
[2] Hong Kong Univ Sci & Technol, Biotechnol Res Inst, Kowloon, Hong Kong, Peoples R China
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 17期
关键词：
D O I：
10.1021/ol0263191
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHIC] Head-to-tail cyclization of peptides is a multistep process involving tedious C-terminal activation and side chain protection. Here we report a facile, quantitative cyclization method in aqueous ammonia solution for the total syntheses of the cyclic decapeptide antibiotic Tyrocidine A and its analogues from their fully deprotected linear thioester precursors on a solid support. This novel aqueous method is conformation-dependent and may be applicable to syntheses of other natural cyclic peptides.
引用
收藏
页码：2893 / 2895
页数：3
相关论文
共 21 条
[1]   DESIGN OF MODEL AMPHIPATHIC PEPTIDES HAVING POTENT ANTIMICROBIAL ACTIVITIES [J].
BLONDELLE, SE ;
HOUGHTEN, RA .
BIOCHEMISTRY, 1992, 31 (50) :12688-12694
[2]   An improved deblocking agent for direct Fmoc solid-phase synthesis of peptide thioesters [J].
Bu, XZ ;
Xie, GY ;
Law, CW ;
Guo, ZH .
TETRAHEDRON LETTERS, 2002, 43 (13) :2419-2422
[3]   Peptide helicity and membrane surface charge modulate the balance of electrostatic and hydrophobic interactions with lipid bilayers and biological membranes [J].
Dathe, M ;
Schumann, M ;
Wieprecht, T ;
Winkler, A ;
Beyermann, M ;
Krause, E ;
Matsuzaki, K ;
Murase, O ;
Bienert, M .
BIOCHEMISTRY, 1996, 35 (38) :12612-12622
[4]   Hydrophobicity, hydrophobic moment and angle subtended by charged residues modulate antibacterial and haemolytic activity of amphipathic helical peptides [J].
Dathe, M ;
Wieprecht, T ;
Nikolenko, H ;
Handel, L ;
Maloy, WL ;
MacDonald, DL ;
Beyermann, M ;
Bienert, M .
FEBS LETTERS, 1997, 403 (02) :208-212
[5]   Peptide antibiotics [J].
Hancock, REW .
LANCET, 1997, 349 (9049) :418-422
[6]   POSSIBLE MOLECULAR MODELS FOR GRAMICIDIN-S AND THEIR RELATIONSHIP TO PRESENT IDEAS OF PROTEIN STRUCTURE [J].
HODGKIN, DC ;
OUGHTON, BM .
BIOCHEMICAL JOURNAL, 1957, 65 (04) :752-756
[7]   SYNTHESIS OF BIOLOGICALLY-ACTIVE CYCLIC-PEPTIDES [J].
IZUMIYA, N ;
KATO, T ;
WAKI, M .
BIOPOLYMERS, 1981, 20 (09) :1785-1791
[8]  
Izumiya N., 1979, SYNTHETIC ASPECTS BI
[9]  
JI AX, 1983, INT J PEPT PROT RES, V22, P590
[10]   Dissociation of antimicrobial and hemolytic activities in cyclic peptide diastereomers by systematic alterations in amphipathicity [J].
Kondejewski, LH ;
Jelokhani-Niaraki, M ;
Farmer, SW ;
Lix, B ;
Kay, CM ;
Sykes, BD ;
Hancock, REW ;
Hodges, RS .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (19) :13181-13192
123