Fmoc chemistry compatible thio-ligation assembly of proteins

被引:24
作者
Biancalana, S
Hudson, D
Songster, MF
Thompson, SA
机构
[1] Biosearch Technol Inc, Novato, CA 94949 USA
[2] Berlex Biosci, Richmond, CA 94804 USA
来源
LETTERS IN PEPTIDE SCIENCE | 2000年 / 7卷 / 05期
关键词
chemoselective ligation; Fmoc-methodology; iso-thiouronium salts; Kenner safety catch resin; native chemical ligation; peptide thioesters; peptide isomerisation; safety-catch linkers; solid-phase synthesis; thioester exchange;
D O I
10.1023/A:1011849912229
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
We describe, and compare, two methods which enable the assembly of proteins from peptide thioester fragments prepared by Fmoc chemistry mediated solid phase synthesis. The first, which utilizes iso-thiouronium salts, allows formation of thiophenyl esters directly from partially protected peptides, either in solution or on resin. The second uses `sulfonamide' based safety-catch resins. Data on yields, generality and potential for side-reactions are provided.
引用
收藏
页码:291 / 297
页数:7
相关论文
共 11 条
[1]   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
[2]   An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].
Backes, BJ ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330
[3]   2-mercaptopyridone 1-oxide-based uronium salts:: New peptide coupling reagents [J].
Bailén, MA ;
Chinchilla, R ;
Dodsworth, DJ ;
Nájera, C .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8936-8939
[4]   SYNTHESEN MIT AMIDCHLORIDEN .3. SYNTHESE UND REAKTIONEN VON CHLORFORMAMIDINIUMCHLORIDEN [J].
EILINGSFELD, H ;
WEIDINGER, H ;
SEEFELDER, M ;
NEUBAUER, G .
CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (05) :1232-&
[5]   S-(1-oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium hexafluorophosphate.: A new reagent for preparing hindered Barton esters [J].
Garner, P ;
Anderson, JT ;
Dey, S ;
Youngs, WJ ;
Galat, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :5732-5733
[6]  
GAUBE A, 1977, LIEBIGS ANN CHEM, P859
[7]   Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry [J].
Ingenito, R ;
Bianchi, E ;
Fattori, D ;
Pessi, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11369-11374
[8]   SAFETY CATCH PRINCIPLE IN SOLID PHASE PEPTIDE SYNTHESIS [J].
KENNER, GW ;
MCDERMOT.JR ;
SHEPPARD, RC .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (12) :636-&
[9]  
Muir TW, 1997, METHOD ENZYMOL, V289, P266
[10]   Fmoc-based synthesis of peptide-αthioesters:: Application to the total chemical synthesis of a glycoprotein by native chemical ligation [J].
Shin, Y ;
Winans, KA ;
Backes, BJ ;
Kent, SBH ;
Ellman, JA ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (50) :11684-11689