A One-Pot Saponification-Coupling Sequence Suitable for C-Terminus Peptide Elongation Using Lithium Carboxylates

被引：1
作者：
Azzouz, Rabah
Petit, Sylvain
Rouchet, Jean-Baptiste
Bischoff, Laurent [1 ]
机构：
[1] Univ Rouen, Normandie Univ, COBRA, UMR 6014,INSA Rouen,CNRS,IRCOF, F-76821 Mont St Aignan, France
来源：
SYNLETT | 2014年 / 25卷 / 13期
关键词：
lithium carboxylate; peptide coupling; amide; amino acid; epimerization; AMIDE BOND FORMATION; RACEMIZATION; REAGENTS;
D O I：
10.1055/s-0034-1378330
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient procedure has been developed for the saponification of common peptide esters, followed by straightforward coupling of the lithium carboxylate. Adding some water to the reaction medium gave faster saponification and did not interfere with the coupling reagent. As peptide chemistry constitutes a major application of the amidation reaction, amino acid substrates were chosen for this study, monitoring both yields and epimerization of the peptides obtained.
引用
收藏
页码：1843 / 1846
页数：4
相关论文
共 14 条
[1]   Carbonyl complexes of chromium, molybdenum and tungsten with isocyano acetate.: Reactions of coordinated isocyanoacetate.: Stabilization of isocyanoacetic acid and isocyanoacetyl chloride at the metal atom.: Isocyanopeptides [J].
Achatz, D ;
Lang, MA ;
Völkl, A ;
Fehlhammer, WP ;
Beck, W .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2005, 631 (12) :2339-2346
[2]   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
[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]   General and Scalable Amide Bond Formation with Epimerization-Prone Substrates Using T3P and Pyridine [J].
Dunetz, Joshua R. ;
Xiang, Yanqiao ;
Baldwin, Aaron ;
Ringling, Justin .
ORGANIC LETTERS, 2011, 13 (19) :5048-5051
[5]   Peptide Coupling Reagents, More than a Letter Soup [J].
El-Faham, Ayman ;
Albericio, Fernando .
CHEMICAL REVIEWS, 2011, 111 (11) :6557-6602
[6]  
Evans D.A., 1982, Aldrichimica Acta, V15, P23
[7]   Amidation Reactions from the Direct Coupling of Metal Carboxylate Salts with Amines [J].
Goodreid, Jordan D. ;
Duspara, Petar A. ;
Bosch, Caroline ;
Batey, Robert A. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) :943-954
[8]  
GRIEHL C, 1994, HRC-J HIGH RES CHROM, V17, P700
[9]  
Llanes Garcia. A. L., 2007, SYNLETT, P1328
[10]   Amide bond formation and peptide coupling [J].
Montalbetti, CAGN ;
Falque, V .
TETRAHEDRON, 2005, 61 (46) :10827-10852
12