Premium
FeCl 3 ‐Mediated Boc Deprotection: Mild Facile Boc‐Chemistry in Solution and on Resin
Author(s) -
Giri Rajat S.,
Roy Sayanta,
Dolai Gobinda,
Manne Srinivasa R.,
Mandal Bhubaneswar
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904617
Subject(s) - chemistry , amino acid , peptide synthesis , reagent , peptide , peptide bond , combinatorial chemistry , protecting group , oligopeptide , solid phase synthesis , amide , yield (engineering) , organic chemistry , materials science , biochemistry , alkyl , metallurgy
A mild, practical, and straight forward method for Boc deprotection and its use in peptide synthesis both in solution and on solid support is presented. Boc protecting group is removed from the N‐terminal amino acid of the amino acid and the peptide using environment‐friendly cost‐effective Lewis acid, FeCl 3 . The deprotected amino group undergoes C−N bond formation with the next Boc‐protected amino acid in the presence of a suitable coupling reagent and base. A library of di‐ to tetrapeptides is synthesized with moderate to good yield from standard and nonstandard Boc‐protected amino acids in solution. Most importantly, this protocol can be used for the solid‐phase peptide synthesis (SPPS) using Boc‐protected amino acids on the acid‐sensitive Rink amide resin, which is usually used for Fmoc chemistry. This protocol thus allows practicing Boc chemistry in a greener manner, and on‐demand switching from Fmoc to Boc chemistry and vice‐versa while synthesizing one oligopeptide on the same resin. The inherent orthogonality of Fmoc and Boc chemistry allows facile synthesis of branched and cyclized peptides on the resin as well.