Efficient loading of sulfonamide safety-catch linkers by Fmoc amino acid fluorides

被引:32
作者
Ingenito, R [1 ]
Dreznjak, D [1 ]
Guffler, S [1 ]
Wenschuh, H [1 ]
机构
[1] Jerini AG, D-12489 Berlin, Germany
关键词
D O I
10.1021/ol0256320
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Fmoc-protected amino acid fluorides were found to be excellent reagents for the acylation of sulfonamide safety-catch linkers (SCL) suitable for the subsequent preparation of peptide C-terminal thioesters. High loadings were obtained on different types of resins with low levels of epimerization.
引用
收藏
页码:1187 / 1188
页数:2
相关论文
共 11 条
[1]   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
[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]   ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID FLUORIDES - CONVENIENT NEW PEPTIDE COUPLING REAGENTS APPLICABLE TO THE FMOC/TERT-BUTYL STRATEGY FOR SOLUTION AND SOLID-PHASE SYNTHESES [J].
CARPINO, LA ;
SADATAALAEE, D ;
CHAO, HG ;
DESELMS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9651-9652
[4]   ESTERIFICATION OF CARBOXYLIC-ACIDS USING BOP OR PYBOP [J].
COSTE, J ;
CAMPAGNE, JM .
TETRAHEDRON LETTERS, 1995, 36 (24) :4253-4256
[5]   Racemization studies of Fmoc-Ser(tBu)-OH during stepwise continuous-flow solid-phase peptide synthesis [J].
Di Fenza, A ;
Tancredi, M ;
Galoppini, C ;
Rovero, P .
TETRAHEDRON LETTERS, 1998, 39 (46) :8529-8532
[6]   EFFICIENT ACYLATION OF HYDROXY FUNCTIONS BY MEANS OF FMOC AMINO-ACID FLUORIDES [J].
GRANITZA, D ;
BEYERMANN, M ;
WENSCHUH, H ;
HABER, H ;
CARPINO, LA ;
TRURAN, GA ;
BIENERT, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) :2223-2224
[7]   Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis [J].
Han, YX ;
Albericio, F ;
Barany, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4307-4312
[8]   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
[9]  
KADUK C, 1995, LETT PEPT SCI, V2, P285, DOI DOI 10.1007/BF00142240
[10]   BOP AS A REAGENT FOR MILD AND EFFICIENT PREPARATION OF ESTERS [J].
KIM, MH ;
PATEL, DV .
TETRAHEDRON LETTERS, 1994, 35 (31) :5603-5606