Sun Cheng Jun, Srivastava Aasheesh, Reifert Jack R, Waite J Herbert
Molecular, Cell & Developmental Biology Department, University of California at Santa Barbara, Santa Barbara, CA, USA.
J Adhes. 2009 Feb 1;85(2-3):126. doi: 10.1080/00218460902782188.
The sandcastle worm Phragmatopoma californica, a marine polychaete, constructs a tube-like shelter by cementing together sand grains using a glue secreted from the building organ in its thorax. The glue is a mixture of post-translationally modified proteins, notably the cement proteins Pc-1 and Pc-2 with the amino acid, 3,4-dihydroxyphenyl-L-alanine (DOPA). Significant amounts of a halogenated derivative of DOPA were isolated from the worm cement following partial acid hydrolysis and capture of catecholic amino acids by phenylboronate affinity chromatography. Analysis by tandem mass spectrometry and (1)H NMR indicates the DOPA derivative to be 2-chloro-4, 5-dihydroxyphenyl-L-alanine. The potential roles of 2-chloro-DOPA in chemical defense and underwater adhesion are considered.
加州刺胞曲壳虫（Phragmatopoma californica）是一种海洋多毛纲动物，它利用胸部构建器官分泌的胶水将沙粒黏合在一起，建造出管状庇护所。这种胶水是翻译后修饰蛋白质的混合物，特别是含有氨基酸3,4-二羟基苯丙氨酸（DOPA）的黏合蛋白Pc-1和Pc-2。在部分酸水解并用苯基硼酸亲和色谱法捕获儿茶酚氨基酸后，从虫胶中分离出了大量DOPA的卤代衍生物。串联质谱分析和¹H NMR分析表明，该DOPA衍生物为2-氯-4,5-二羟基苯丙氨酸。文中探讨了2-氯-DOPA在化学防御和水下黏附中的潜在作用。
