Halogenated DOPA in a Marine Adhesive Protein.

The Journal of Adhesion
Cheng Jun SunJ H Waite

Abstract

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.

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Citations

Nov 8, 2011·Annual Review of Materials Research·Bruce P LeeJ H Waite
Nov 13, 2015·Chemistry : a European Journal·Marie KrogsgaardHenrik Birkedal
Apr 27, 2018·Chemical Society Reviews·Danielle M Raymond, Bradley L Nilsson
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Mar 5, 2019·Chembiochem : a European Journal of Chemical Biology·Nediljko Budisa, Tobias Schneider
Dec 6, 2016·Journal of Polymer Science. Part A, Polymer Chemistry·Pegah Kord Forooshani, Bruce P Lee
Nov 10, 2012·Advanced Materials·Luis García-FernándezAránzazu del Campo
Jan 27, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Seyedehfatemeh RazaviamriBruce P Lee
Dec 23, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Yiwen XuJinghong Ma
Nov 10, 2021·Chemical Society Reviews·Amal NarayananAbraham Joy

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Methods Mentioned

BETA
NMR

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