Solid‐Phase Synthesis of the Peptaibol Alamethicin U‐22324 by Using a Double‐Linker Strategy

Abstract

The facile Fmoc (Fluorenylmethoxycarbonyl) solid‐phase synthesis of the α‐helical‐channel‐forming peptaibol alamethicin U‐22324 is described. A late‐stage reduction by using a new double‐linker method was used to introduce the C‐terminal alcohol. Furthermore, we also report the synthesis of an alamethicin analogue with a C‐terminal carboxylic acid.

Amphiphilic polypeptides with prolonged enzymatic stability for the preparation of self-assembled nanobiomaterials

“…27 A range of publications reported the synthesis of Aib-containing peptides via solution 22,[31][32][33] or solid-phase techniques. 21,[34][35][36][37] Recently, Tsuchiya and Numata described also the enzymatic synthesis of hydrophobic polypeptides based on Ala and Aib. 38 On the contrary to the short Aib peptides, the preparation of long polypeptides with multiple Aib residues is complicated because of the sterical hindrance of the Aib residue.…”

Recent Progress in Solid‐Phase Total Synthesis of Naturally Occurring Small Peptides

“…Additionally, the terminal amino alcohol also could be formed by reduction of an amino acid ester which is attached on an electrondeficient linker (e. g. 4-hydroxymethylbenzoic acid, (HMBA)), such as the synthesis of peptaibol alamethicin U-22324 (48, Scheme 6). [56] Microcin B17 (MccB17, 49, Scheme 7) is a modified small linear peptide with 43 amino acid residues. The mature microcin B17 contains four thiazoles and four oxazoles which are resulted from post-translational modification of four serine residues and four cysteine residues.…”

“…Additionally, the terminal amino alcohol also could be formed by reduction of an amino acid ester which is attached on an electron‐deficient linker (e. g. 4‐hydroxymethylbenzoic acid, (HMBA)), such as the synthesis of peptaibol alamethicin U‐22324 ( 48 , Scheme 6). [56] …”

Molecular methods unravel the biosynthetic potential of Trichoderma species

“…Peptaibols are a group of fungal peptides biosynthesized by nonribosomal peptide synthetases (NRPS), such as the antibiotic polypeptide alamethicin 3, the rst peptaibol isolated in 1967 from T. viride, a strain that was later reidentied as T. arundinaceum. 27,[36][37][38][39][40] Fungal polyketides and nonribosomal peptides are produced by highly programmed megasynth(et)ases named polyketide synthases (PKS) and non-ribosomal peptide synthetases (NRPS), respectively. [41][42][43] Trichoderma spp.…”