Synthesis of proteins by native chemical ligation using Fmoc-based chemistry

被引:37
作者
Camarero, JA [1 ]
Mitchell, AR [1 ]
机构
[1] Lawrence Livermore Natl Lab, Chem Biol & Nucl Sci Div, Livermore, CA 94550 USA
关键词
chemical protein synthesis; Native Chemical Ligation; peptide alpha-thioester; hydrazine linker; protein engineering; Fmoc-chemistry;
D O I
10.2174/0929866054864166
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
C-terminal peptide alpha-thioesters are valuable intermediates in the synthesis/semisynthesis of proteins by native chemical. ligation. They are prepared either by solid-phase peptide synthesis (SPPS) or biosynthetically by protein splicing techniques. The present paper reviews the different methods available for the chemical synthesis of peptide alpha-thioesters using Fmoc-based SPPS.
引用
收藏
页码:723 / 728
页数:6
相关论文
共 78 条
[1]   Solid-phase synthesis of C-terminal modified peptides [J].
Alsina, J ;
Albericio, F .
BIOPOLYMERS, 2003, 71 (04) :454-477
[2]   Backbone amide linker (BAL) strategy for Nα-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters [J].
Alsina, J ;
Yokum, TS ;
Albericio, F ;
Barany, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8761-8769
[3]   Protein backbone engineering through total chemical synthesis: New insight into the mechanism of HIV-1 protease catalysis [J].
Baca, M ;
Kent, SBH .
TETRAHEDRON, 2000, 56 (48) :9503-9513
[4]   Activation method to prepare a highly reactive acylsulfonamide ''safety-catch'' linker for solid-phase synthesis [J].
Backes, BJ ;
Virgilio, AA ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3055-3056
[5]   An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].
Backes, BJ ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330
[6]   A latent aryl hydrazine 'safety-catch' linker compatible with N-alkylation [J].
Berst, F ;
Holmes, AB ;
Ladlow, M ;
Murray, PJ .
TETRAHEDRON LETTERS, 2000, 41 (34) :6649-6653
[7]   Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters [J].
Brask, J ;
Albericio, F ;
Jensen, KJ .
ORGANIC LETTERS, 2003, 5 (16) :2951-2953
[8]  
Camarero JA, 1998, J PEPT RES, V51, P303
[9]   Fmoc-based synthesis of peptide α-thioesters using an aryl hydrazine support [J].
Camarero, JA ;
Hackel, BJ ;
de Yoreo, JJ ;
Mitchell, AR .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (12) :4145-4151
[10]  
Camarero JA, 1998, ANGEW CHEM INT EDIT, V37, P347, DOI 10.1002/(SICI)1521-3773(19980216)37:3<347::AID-ANIE347>3.0.CO