Solution-phase-peptide synthesis via the group-assisted purification (GAP) chemistry without using chromatography and recrystallization

Abstract

The solution phase synthesis of N-protected amino acids and peptides has been achieved through the Group-Assisted Purification (GAP) chemistry by avoiding disadvantages of other methods in regard to the difficult scale-up, expenses of solid and soluble polymers, etc. The GAP synthesis can reduce the use of solvents, silica gels, energy and manpower. In addition, the GAP auxiliary can be conveniently recovered for re-use and is environmentally friendly and benign, and substantially reduces waste production in academic labs and industry.

Scheme 1

GAP protection of L-proline benzyl ester and its deprotection

Scheme 2

GAP protection of L-tyrosine benzyl ester and its deprotection

Scheme 3

GAP synthesis of dipeptides and tripeptides

Scheme 4

GAP synthesis of biphalins