Duality of mechanism in the tetramethylfluoroformamidinium hexafluorophosphate-mediated synthesis of N-benzyloxycarbonylamino acid fluorides

被引：22
作者：
Fiammengo, R
Licini, G
Nicotra, A
Modena, G
Pasquato, L
Scrimin, P
Broxterman, QB
Kaptein, B
机构：
[1] Univ Padua, Dipartimento Chim Organ, I-35131 Padua, Italy
[2] CNR, Ctr Meccanismi Reaz, I-35131 Padua, Italy
[3] DSM Res, Organ Chem & Biotechnol Sect, NL-6160 MD Geleen, Netherlands
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 17期
关键词：
D O I：
10.1021/jo0009393
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[No abstract available]
引用
收藏
页码：5905 / 5910
页数：6
相关论文
共 31 条
[1]  
Benoiton NL, 1996, BIOPOLYMERS, V40, P245
[2]   2-ALKOXY-5(4H)-OXAZOLONES FROM N-ALKOXYCARBONYLAMINO ACIDS AND THEIR IMPLICATION IN CARBODIIMIDE-MEDIATED REACTIONS IN PEPTIDE-SYNTHESIS [J].
BENOITON, NL ;
CHEN, FMF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02) :384-389
[3]  
BOLIN DR, 1989, INT J PEPT PROT RES, V33, P353
[4]   Ground state and transition state contributions to the rates of intramolecular and enzymatic reactions [J].
Bruice, TC ;
Lightstone, FC .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (02) :127-136
[5]   Reactions of charged substrates .4. The gas-phase dissociation of (4-substituted benzyl)dimethylsulfoniums and -pyridiniums [J].
Buckley, N ;
Maltby, D ;
Burlingame, AL ;
Oppenheimer, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2753-2762
[6]   ((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
[7]   Peptide synthesis via amino acid halides [J].
Carpino, LA ;
Beyermann, M ;
Wenschuh, H ;
Bienert, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274
[8]   TETRAMETHYLFLUOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE - A RAPID-ACTING PEPTIDE COUPLING REAGENT FOR SOLUTION AND SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5401-5402
[9]   TERT-BUTYLOXYCARBONYL AND BENZYLOXYCARBONYL AMINO-ACID FLUORIDES - NEW, STABLE RAPID-ACTING ACYLATING AGENTS FOR PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
MANSOUR, EME ;
SADATAALAEE, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2611-2614
[10]  
CLARK JH, 1985, TETRAHEDRON LETT, V26, P2233, DOI 10.1016/S0040-4039(00)98970-6
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