198561-07-8Relevant articles and documents
Design, synthesis and functional analysis of dansylated polytheonamide mimic: An artificial peptide ion channel
Itoh, Hiroaki,Matsuoka, Shigeru,Kreir, Mohamed,Inoue, Masayuki
, p. 14011 - 14018 (2012)
We report herein the design, total synthesis, and functional analysis of a novel artificial ion channel molecule, designated as dansylated polytheonamide mimic (3). The channel 3 was designed based on an exceptionally potent cytotoxin, polytheonamide B (1
pDobz/pDobb protected diaminodiacid as a novel building block for peptide disulfide-bond mimic synthesis
Liu, Chao,Zou, Yan,Hu, Honggang,Jiang, Yunyun,Qin, Luping
, p. 5438 - 5444 (2019/03/02)
The diaminodiacid strategy has been widely studied in the chemical synthesis of peptide disulfide bond mimics. Diaminodiacid building blocks, which are key intermediates, are currently under the spotlight. However, one technical bottleneck inherent in existing building blocks is the contamination problem caused by the heavy metal reagents during the deprotection process, which makes the peptides less suitable for pharmaceutical use. Herein, we describe the successful development of a p-dihydroxyborylbenzyloxycarbonyl pinacol ester (pDobz)- and p-dihydroxyborylbenzyl pinacol ester (pDobb)-based novel diaminodiacid building block that can be easily deprotected via mild treatment with amine oxide. Its efficiency and practicability were also confirmed by the total synthesis of contryphan-Vn disulfide bond mimic. The results suggested that this novel diaminodiacid building block has satisfactory Fmoc SPPS compatibility, yet only required a facile, rapid, and metal-free deprotection process. We believe this novel diaminodiacid building block could promote further development of the diaminodiacid strategy.
Azide- and alkyne-functionalised α- And β3-amino acids
Sminia, Tjerk Jacco,Pedersen, Daniel Sejer
supporting information, p. 2643 - 2646 (2013/01/15)
The synthesis and full characterisation of bifunctional β3-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing β3-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding α-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis. Georg Thieme Verlag KG Stuttgart · New York.
