"O-acyl isopeptide method" for peptide synthesis:: synthesis of forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH

被引:43
作者
Yoshiya, Taku
Taniguchi, Atsuhiko
Sohma, Youhei
Fukao, Fukue
Nakamura, Setsuko
Abe, Naoko
Ito, Nui
Skwarczynski, Mariusz
Kimura, Tooru
Hayashi, Yoshio
Kiso, Yoshiaki [1 ]
机构
[1] Kyoto Pharmaceut Univ, 21st Century COE Program, Ctr Frontier Res Med Sci, Dept Med Chem,Yamashina Ku, Kyoto 6078412, Japan
[2] Kyoto Pharmaceut Univ, 21st Century COE Program, Dept Chem Phys, Kyoto 6078412, Japan
关键词
SEQUENCE-CONTAINING PEPTIDES; BIOLOGY-ORIENTED SYNTHESIS; VIRUS MATRIX PROTEIN; EFFICIENT SYNTHESIS; MIGRATION REACTION; PROTECTING GROUPS; SWITCH-PEPTIDES; CLICK PEPTIDE; RAPID REMOVAL; AMINO-ACIDS;
D O I
10.1039/b702284k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The O-acyl isopeptide method has recently received attention as an efficient synthetic method for peptides. Herein, forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH (1-40) were effectively synthesized in two-steps without epimerization. The O-acyl isodipeptide units are important building blocks to enable the routine use of the O-acyl isopeptide method.
引用
收藏
页码:1720 / 1730
页数:11
相关论文
共 48 条
[1]   Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides [J].
Angell, YM ;
Alsina, J ;
Albericio, F ;
Barany, G .
JOURNAL OF PEPTIDE RESEARCH, 2002, 60 (05) :292-299
[2]  
[Anonymous], J AM CHEM SOC
[3]  
ANWER MK, 1980, SYNTHESIS-STUTTGART, P929
[4]   RACEMIZATION OF ACTIVATED, URETHANE-PROTECTED AMINO-ACIDS BY PARA-DIMETHYLAMINOPYRIDINE - SIGNIFICANCE IN SOLID-PHASE PEPTIDE-SYNTHESIS [J].
ATHERTON, E ;
BENOITON, NL ;
BROWN, E ;
SHEPPARD, RC ;
WILLIAMS, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) :336-337
[5]  
BEDNAREK MA, 1991, J IMMUNOL, V147, P4047
[6]   Synthesis of 'difficult' peptide sequences:: application of a depsipeptide technique to the Jung-Redemann 10- and 26-mers and the amyloid peptide Aβ(1-42) [J].
Carpino, LA ;
Krause, E ;
Sferdean, CD ;
Schümann, M ;
Fabian, H ;
Bienert, M ;
Beyermann, M .
TETRAHEDRON LETTERS, 2004, 45 (40) :7519-7523
[7]   Depsipeptide methodology for solid-phase peptide synthesis:: Circumventing side reactions and development of an automated technique via depsidipeptide units [J].
Coin, Irene ;
Doelling, Rudolf ;
Krause, Eberhard ;
Bienert, Michael ;
Beyermann, Michael ;
Sferdean, Calin Dan ;
Carpino, Louis A. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6171-6177
[8]   ESTERIFICATION OF N-PROTECTED ALPHA-AMINO-ACIDS WITH ALCOHOL/CARBODIIMIDE/4-(DIMETHYLAMINO)-PYRIDINE - RACEMIZATION OF ASPARTIC AND GLUTAMIC-ACID DERIVATIVES [J].
DHAON, MK ;
OLSEN, RK ;
RAMASAMY, K .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1962-1965
[9]   RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE [J].
FELIX, AM ;
HEIMER, EP ;
LAMBROS, TJ ;
TZOUGRAKI, C ;
MEIENHOFER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4194-4196
[10]   USE OF THE N(PI)-PHENACYL GROUP FOR THE PROTECTION OF THE HISTIDINE SIDE-CHAIN IN PEPTIDE-SYNTHESIS [J].
FLETCHER, AR ;
JONES, JH ;
RAMAGE, WI ;
STACHULSKI, AV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09) :2261-2267