On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis

被引：150
作者：
Albericio, F
Cases, M
Alsina, J
Triolo, SA
Carpino, LA
Kates, SA
机构：
[1] UNIV MASSACHUSETTS,DEPT CHEM,AMHERST,MA 01003
[2] PERSEPT BIOSYST INC,FRAMINGHAM,MA 01701
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 27期
关键词：
D O I：
10.1016/S0040-4039(97)01011-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Phosphonium derivatives of HOAt such as PyAOP are useful for the solid-phase preparation of a range of peptides that include those incorporating hindered amino acids, difficult short sequences, and cyclic peptides. An advantage relative to uronium salts is that excess PyAOP does not undergo the detrimental side-reaction at the amino terminus which blocks further chain assembly. (C) 1997 Published by Elsevier Science Ltd.
引用
收藏
页码：4853 / 4856
页数：4
相关论文
共 25 条
[1]   PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].
ALBERICIO, F ;
KNEIBCORDONIER, N ;
BIANCALANA, S ;
GERA, L ;
MASADA, RI ;
HUDSON, D ;
BARANY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3730-3743
[2]  
ALSINA J, 1997, TETRAHEDRON LETT, V38, P4195
[3]   SOLID-PHASE SYNTHESIS OF CYCLOSPORINE PEPTIDES [J].
ANGELL, YM ;
THOMAS, TL ;
FLENTKE, GR ;
RICH, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) :7279-7280
[4]   COMPARATIVE-STUDIES OF THE COUPLING OF N-METHYLATED, STERICALLY HINDERED AMINO-ACIDS DURING SOLID-PHASE PEPTIDE-SYNTHESIS [J].
ANGELL, YM ;
GARCIAECHEVERRIA, C ;
RICH, DH .
TETRAHEDRON LETTERS, 1994, 35 (33) :5981-5984
[5]  
ARTTAMANGKUL S, 1996, LETT PEPT SCI, V3, P357
[6]   POLYAMIDE SUPPORTS FOR POLYPEPTIDE-SYNTHESIS [J].
ATHERTON, E ;
CLIVE, DLJ ;
SHEPPARD, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (22) :6584-6585
[7]   Z-GLN(TRT)-AIB-AIB-AIB-OME SYNTHESIS USING UNCA AND BOP PYBROP COUPLING METHODS [J].
AUVINGUETTE, C ;
FREROT, E ;
COSTE, J ;
REBUFFAT, S ;
JOUIN, P ;
BODO, B .
TETRAHEDRON LETTERS, 1993, 34 (15) :2481-2482
[8]  
BELTON P, 1988, PEPTIDES 1988, P619
[9]   RACEMIZATION STUDIES DURING SOLID-PHASE PEPTIDE-SYNTHESIS USING AZABENZOTRIAZOLE-BASED COUPLING REAGENTS [J].
CARPINO, LA ;
EL-FAHAM, A ;
ALBERICIO, F .
TETRAHEDRON LETTERS, 1994, 35 (15) :2279-2282
[10]   ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
123