Peptide Bond Formation via Nα-Protected Diacyldiselenides

Peptide Bond Formation via Nα-Protected Diacyldiselenides

A simple, straightforward, for the peptide bond formation employing corresponding carboxylic acids and amines derived from amino acids via N α -protected diacyldiselenide is delineated. The key step of the synthesis is the in situ generation of N α -protected diacyldiselenide using NaBH 2 Se 3 as se...

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Veröffentlicht in:International journal of peptide research and therapeutics 2019-06, Vol.25 (2), p.653-658
Hauptverfasser: Vathsala, U., Roopesh Kumar, L., Sagar, N. R., Mahesh, M., Venkata Ramana, P., Sureshbabu, Vommina V.
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Sprache:eng
Schlagworte:
Amines
Amino acids
Animal Anatomy
Biochemistry
Biomedical and Life Sciences
Carboxylic acids
Histology
Life Sciences
Molecular Medicine
Morphology
Peptides
Pharmaceutical Sciences/Technology
Pharmacology/Toxicology
Polymer Sciences
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container_end_page 658
container_issue 2
container_start_page 653
container_title International journal of peptide research and therapeutics
container_volume 25
creator Vathsala, U.
Roopesh Kumar, L.
Sagar, N. R.
Mahesh, M.
Venkata Ramana, P.
Sureshbabu, Vommina V.
description A simple, straightforward, for the peptide bond formation employing corresponding carboxylic acids and amines derived from amino acids via N α -protected diacyldiselenide is delineated. The key step of the synthesis is the in situ generation of N α -protected diacyldiselenide using NaBH 2 Se 3 as selenating reagent, followed by trapping with an amino acid ester leading to the peptide. The formation of N α -protected diacyldiselenide was confirmed through TLC and HRMS analysis using crude sample. The reaction is clean and all the products were obtained in moderate to good yields, including for sterically hindered amino acids. The protocol is free from racemisation, compatible with Fmoc, Cbz and Boc groups. Graphical Abstract
doi_str_mv 10.1007/s10989-018-9711-z
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1573-3904
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subjects Amines
Amino acids
Animal Anatomy
Biochemistry
Biomedical and Life Sciences
Carboxylic acids
Histology
Life Sciences
Molecular Medicine
Morphology
Peptides
Pharmaceutical Sciences/Technology
Pharmacology/Toxicology
Polymer Sciences
title Peptide Bond Formation via Nα-Protected Diacyldiselenides
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