Rapid, Continuous Solution-Phase Peptide Synthesis:  Application to Peptides of Pharmaceutical Interest

Abstract

The Fmoc/TAEA and Bsmoc/TAEA methods for the rapid, continuous solution synthesis of peptide segments are shown to be applicable to the gram-scale synthesis of short peptides as well as, for the first time, to the synthesis of a relatively long (22-mer) segment, (hPTH 13-34). In the latter case the crude product was of significantly greater purity than a sample obtained via a solid-phase protocol. The Bsmoc methodology was optimized by a new technique involving filtration of the growing partially deprotected peptide at each couplingdeprotection cycle through a short column of silica gel.

Amino Acid-Protecting Groups

“…73,74 Bsmoc-amino acids have been used to synthesize several model peptides in which the Bsmoc group was removed with 2-5 % piperidine in DMF, 70 and have shown better performance than Fmoc amino acids in difficult couplings such as Aib-Aib. 41 Furthermore, the Bsmoc group can be selectively removed with 2% of tris(2-aminoethyl)amine (TAEA) in DCM in the presence of Fm esters.…”

Increasing bacterial affinity and cytocompatibility with four-arm star glycopolymers and antimicrobial α-polylysine

“…Among the conventional well-established techniques to prepare synthetic peptides, solution-coupling and solidphase syntheses provide precise control over chain composition, with the drawback of employing multistep procedures in a tedious, time-consuming and expensive manner. [10][11][12] In technique allows the preparation of polypeptides with a narrowly defined chain length and intrachain composition. 14 Polypeptides consisting of a combination of lysine, alanine, phenylalanine, and leucine amino acids were prepared via the NCA-ROP technique, and the synthetic polypeptides showed microbiocidal activity against a wide range of pathogenic microorganisms, including clinically significant bacteria Serratia marcescens and fungi Candida albicans.…”

Stereoselective 11C Labeling of a “Native” Tetrapeptide by Using Asymmetric Phase‐Transfer Catalyzed Alkylation Reactions

“…[24] In the final step to obtain precursors 7 and 22, free N-terminal amines were converted into the Schiff base by reaction with a benzophenone imine. Peptide side chains were acid labile tert-butoxycarbonyl (Boc)/tBu protected for compatibility with PTC alkylation and rapid deprotection of the final 11 Clabeled product.…”