Abstract
1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz), a readily available and bench stable benziodoxole-based iodine(III) reagent, can be employed for the synthesis of dipeptides from various standard and sterically hindered amino acids in the presence of (4-MeOC6H4)3P. The combined system of IBA-OBz/(4-MeOC6H4)3P is also successfully applied to the solid-phase peptide synthesis and a pentapeptide leu-enkephalin in unprotected form has been synthesized. Density functional theory calculations reveal that the rate-limiting step is nucleophilic attack of 4-dimethylaminopyridine (DMAP) onto IBA-OBz.
Highlights
In 2012, we first reported that iodosodilactone, a bicyclic benziodoxole compound, could function as a coupling reagent to promote the efficient syntheses of esters, macrocyclic lactones, amides, and peptides in the presence of PPh3 at 60o C (Scheme 1) (Tian et al, 2012)
FPID can be readily regenerated after reaction, and iodosodilactone shares the same feature, which is not provided in the existing peptide coupling reagents (Constable et al, 2007; EI-Faham and Albericio, 2011)
We reported that an efficient preparation of IBA-OBz and its synthetic utility as an efficient coupling reagent to promote the synthesis of dipeptides and the solid-phase peptide synthesis of a pentapeptide leu-enkephalin. (Scheme 1C)
Summary
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China, 2 Computational Center for Molecular Science, Nankai. Specialty section: This article was submitted to Organic Chemistry, a section of the journal. Iodine(III) Compound Functioning as a Peptide Coupling Reagent. 1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz), a readily available and bench stable benziodoxole-based iodine(III) reagent, can be employed for the synthesis of dipeptides from various standard and sterically hindered amino acids in the presence of (4-MeOC6 H4 ) P. The combined system of IBA-OBz/(4-MeOC6 H4 ) P is successfully applied to the solid-phase peptide synthesis and a pentapeptide leu-enkephalin in unprotected form has been synthesized. Density functional theory calculations reveal that the rate-limiting step is nucleophilic attack of 4-dimethylaminopyridine (DMAP)
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