State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
J Am Chem Soc. 2010 Nov 24;132(46):16324-6. doi: 10.1021/ja106571g. Epub 2010 Nov 3.
The carboxyl-terminal amide group has been often found in many bioactive peptide natural products, including nosiheptide belonging to the over 80 entity-containing thiopeptide family. Upon functional characterization of a novel protein NosA in nosiheptide biosynthesis, herein we report an unusual C-terminal amide forming strategy in general for maturating certain amide-terminated thiopeptides by processing their precursor peptides featuring a serine extension. NosA acts on an intermediate bearing a bis-dehydroalanine tail and catalyzes an enamide dealkylation to remove the acrylate unit originating from the extended serine residue.
羧基末端酰胺基团经常存在于许多生物活性肽天然产物中，包括属于超过 80 个实体的硫肽家族的诺西肽。在对新型蛋白 NosA 在诺西肽生物合成中的功能进行表征后，本文报道了一种在成熟某些酰胺端硫肽时的不寻常的 C 末端酰胺形成策略，该策略通过对具有丝氨酸延伸的前体肽进行加工来实现。NosA 作用于带有双脱氢丙氨酸尾巴的中间体，并催化烯酰胺脱烷基化，以去除来自延伸丝氨酸残基的丙烯酸盐单元。
