Issue 10, 2019

2D green SPPS: green solvents for on-resin removal of acid sensitive protecting groups and lactamization

Abstract

Aiming at greener synthesis of complex peptides we report that conventional one-dimensional (1D) green solid-phase peptide synthesis (SPPS) is elevated to a two-dimensional (2D) concept in which side chains in peptide resins are functionalized by suitable green tactics. Specifically, we disclose on-resin deblocking using trifluoroacetic acid (TFA)/triisopropylsilane (TIS) in EtOAc/MeCN used in a synthesis of a melanocortin receptor agonist comprising (i) 1D green SPPS (ii) 2D green SPPS by an on-resin TFA/TIS in EtOAc/MeCN deprotection of Lys(Mtt) and Asp(O-2-PhiPr) followed by a lactamization using PyBOP/DIEA in NBP/EtOAc (iii) TFA cleavage followed by green precipitation using 4-methyltetrahydropyran (MTHP)/n-heptane. A further application for our green deprotection protocol was found in peptide fragment cleavages off CTC resins.

Graphical abstract: 2D green SPPS: green solvents for on-resin removal of acid sensitive protecting groups and lactamization

Supplementary files

Article information

Article type
Communication
Submitted
15 Mar 2019
Accepted
23 Apr 2019
First published
30 Apr 2019

Green Chem., 2019,21, 2594-2600

2D green SPPS: green solvents for on-resin removal of acid sensitive protecting groups and lactamization

J. Pawlas, B. Antonic, M. Lundqvist, T. Svensson, J. Finnman and J. H. Rasmussen, Green Chem., 2019, 21, 2594 DOI: 10.1039/C9GC00898E

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