EFFICIENT COUPLING OF ALPHA,ALPHA-DIMETHYL AMINO-ACID USING A NEW CHLORO IMIDAZOLIDIUM REAGENT, CIP

被引:70
作者
AKAJI, K [1 ]
KURIYAMA, N [1 ]
KISO, Y [1 ]
机构
[1] KYOTO PHARMACEUT UNIV,DEPT MED CHEM,YAMASHIMA KU,KYOTO 607,JAPAN
关键词
D O I
10.1016/S0040-4039(00)76895-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CIP (2-chloro-1,3-dimethylimidazolidium hexafluorophosphate) was an efficient coupling agent for N-alpha-protected alpha-aminoisobutyric acid (Aib) in the presence of an additive. The reactivity was enhanced markedly by a catalytic amount of additive in the order of HOAt similar to HODhbt>DMAP>HOBt. These couplings occurred without detectable racemization.
引用
收藏
页码:3315 / 3318
页数:4
相关论文
共 10 条
[1]   ANCHORING OF FMOC AMINO-ACID TO 4-ALKOXYBENZYL ALCOHOL RESIN USING A NEW ESTERIFICATION REAGENT [J].
AKAJI, K ;
KURIYAMA, N ;
KIMURA, T ;
FUJIWARA, Y ;
KISO, Y .
TETRAHEDRON LETTERS, 1992, 33 (22) :3177-3180
[2]   SELF-INDICATING ACTIVATED ESTERS FOR USE IN SOLID-PHASE PEPTIDE-SYNTHESIS - FLUORENYLMETHOXYCARBONYLAMINO ACID-DERIVATIVES OF 3-HYDROXY-4-OXODIHYDROBENZOTRIAZINE [J].
ATHERTON, E ;
CAMERON, L ;
MELDAL, M ;
SHEPPARD, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (24) :1763-1765
[3]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[4]   PYBOP AND PYBROP - 2 REAGENTS FOR THE DIFFICULT COUPLING OF THE ALPHA,ALPHA-DIALKYL AMINO-ACID, AIB [J].
FREROT, E ;
COSTE, J ;
PANTALONI, A ;
DUFOUR, MN ;
JOUIN, P .
TETRAHEDRON, 1991, 47 (02) :259-270
[5]   N-METHYL N-CARBOXYANHYDRIDE - AN UNEXPECTED BY-PRODUCT WHEN COUPLING BOC-N-METHYL AMINO-ACIDS [J].
FREROT, E ;
COSTE, J ;
PONCET, J ;
JOUIN, P ;
CASTRO, B .
TETRAHEDRON LETTERS, 1992, 33 (20) :2815-2816
[6]   FURTHER-STUDIES ON THE SYNTHESIS OF SYMMETRICAL ANHYDRIDES AND 2,4-DISUBSTITUTED-5(4H)-OXAZOLONES FROM N-ALKOXYCARBONYLAMINO ACIDS USING SOLUBLE CARBODIIMIDE [J].
PAQUET, A ;
CHEN, FMF ;
BENOITON, NL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (07) :1335-1338
[7]   USE OF N-FMOC AMINO-ACID CHLORIDES AND ACTIVATED 2-(FLUORENYLMETHOXY)-5(4H)-OXAZOLONES IN SOLID-PHASE PEPTIDE-SYNTHESIS - EFFICIENT SYNTHESES OF HIGHLY N-ALKYLATED CYCLIC HEXAPEPTIDE OXYTOCIN ANTAGONISTS RELATED TO L-365,209 [J].
PERLOW, DS ;
ERB, JM ;
GOULD, NP ;
TUNG, RD ;
FREIDINGER, RM ;
WILLIAMS, PD ;
VEBER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) :4394-4400
[8]   EMERIMICIN-III AND EMERIMICIN-IV AND THEIR ETHYLALANINE(12) EPIMERS - FACILITATED CHEMICAL ENZYMATIC-SYNTHESIS AND A QUALITATIVE EVALUATION OF THEIR SOLUTION STRUCTURES [J].
SLOMCZYNSKA, U ;
BEUSEN, DD ;
ZABROCKI, J ;
KOCIOLEK, K ;
REDLINSKI, A ;
REUSSER, F ;
HUTTON, WC ;
LEPLAWY, MT ;
MARSHALL, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4095-4106
[9]  
SPENCER JR, 1992, INT J PEPT PROT RES, V40, P282
[10]   EFFICIENT SOLID-PHASE ASSEMBLY OF PEPTIDES BEARING CONTIGUOUS HIGHLY HINDERED AIB RESIDUES VIA FMOC AIB FLUORIDE [J].
WENSCHUH, H ;
BEYERMANN, M ;
KRAUSE, E ;
CARPINO, LA ;
BIENERT, M .
TETRAHEDRON LETTERS, 1993, 34 (23) :3733-3736