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A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent.

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.

SUBMITTER: Qiu LJ

PROVIDER: S-EPMC7093377 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent.

Qiu Li-Jun LJ Liu Dan D Zheng Ke K Zhang Ming-Tao MT Zhang Chi C

Frontiers in chemistry 20200318

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 h ...[more]

PMID: 32258000

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