School of Chemical Sciences, The University of Auckland, 23 Symonds St., Auckland 1010, New Zealand.
School of Biological Sciences, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds St., Auckland 1010, New Zealand.
Org Biomol Chem. 2020 Apr 15;18(15):2838-2844. doi: 10.1039/d0ob00203h.
Naturally occurring cyclic lipopeptides exhibit a diverse range of biological activities and possess several favourable properties. Chemically synthesising and modifying these natural compounds can alter their biological and physical properties. Cyclic lipopeptides are often difficult to synthesise, especially when the lipid moiety is directly attached to the cyclic scaffold. The construction of a series of cyclic lipopeptide analogues of the antifungal peptide iturin A is reported herein. The synthesis of the parent peptide macrocycle was achieved using native chemical ligation (NCL), whereupon the regenerated free thiol was used to attach a lipid moiety using Cysteine Lipidation on a Peptide or Amino acid (CLipPA) technology.
天然环脂肽表现出多种多样的生物活性，并具有多种有利的性质。化学合成和修饰这些天然化合物可以改变它们的生物和物理性质。环脂肽通常很难合成，尤其是当脂质部分直接连接到环支架上时。本文报道了抗真菌肽iturin A 的一系列环脂肽类似物的构建。使用天然化学连接（NCL）合成了母体肽大环，然后使用半胱氨酸脂质化在肽或氨基酸上（CLipPA）技术将再生的游离巯基连接到脂质部分上。
