Acosta Gerardo A, Murray Laura, Royo Miriam, de la Torre Beatriz G, Albericio Fernando
CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona (UB), Barcelona, Spain.
Department of Organic Chemistry, University of Barcelona, Barcelona, Spain.
Front Chem. 2020 Apr 22;8:298. doi: 10.3389/fchem.2020.00298. eCollection 2020.
Cyclic depsipeptides constitute a fascinating class of natural products. Most of them are characterized by an ester formed between the β-hydroxy function of Ser/Thr -and related amino acids- and the carboxylic group of the -terminal amino acid. Less frequent are those where the thiol of Cys is involved rendering a thioester (cyclo thiodepsipeptides) and even less common are the cyclo depsipeptides with a phenyl ester coming from the side-chain of Tyr. Herein, the preparation of the later through a cyclative cleavage using the Fmoc-MeDbz/MeNbz-resin is described. This resin has previously reported for the synthesis of cyclo thiodepsipeptides and homodetic peptides. The use of that resin for the preparation of all these peptides is also summarized.
环缩肽是一类引人入胜的天然产物。它们中的大多数的特征是在丝氨酸/苏氨酸（以及相关氨基酸）的β-羟基官能团与末端氨基酸的羧基之间形成酯键。较少见的是那些涉及半胱氨酸硫醇形成硫酯的情况（环硫缩肽），而来自酪氨酸侧链的苯酯的环缩肽则更为罕见。本文描述了通过使用Fmoc-MeDbz/MeNbz树脂进行环化裂解来制备后者的方法。该树脂先前已报道用于环硫缩肽和同系肽的合成。还总结了使用该树脂制备所有这些肽的情况。
