Protein Functionalization Revised: N‐tert‐butoxycarbonylation as an Elegant Tool to Circumvent Protein Crosslinking. Issue 15 (18th June 2014)

• Record Type: Journal Article
• Authors: Van Nieuwenhove, Ine; Stubbe, Birgit; Graulus, Geert‐Jan; Van Vlierberghe, Sandra; Dubruel, Peter
• Is Part Of: Macromolecular rapid communications. Volume 35:Issue 15(2014:Aug.)
• Page Start: 1351
• Page End: 1355
• Publication Date: 2014-06-18
• Subjects: Macromolecules -- Periodicals; Polymers -- Periodicals; Chemistry -- Periodicals; 547.705
• DOI: 10.1002/marc.201400103
• Languages: English
• ISSNs: 1022-1336

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>The protection of primary amines available in proteins holds great potential to introduce a plethora of diverse functionalities along the protein backbone (e.g., via its carboxylic acid or alcohol moieties) while circumventing the crosslinking issue using conventional approaches. This paper reports on a straightforward and efficient proof‐of‐concept including the chemoselective <italic>N‐tert</italic>‐butyloxycarbonylation of the primary amines in the protein gelatin (gel‐NH‐BOC), followed by introducing crosslinkable methacrylamide moieties. The reaction is performed successfully under relatively mild conditions (50 °C). Following selective protein functionalization, the deprotection is realized by adding a catalytic amount of an aqueous hydrogen chloride solution. The present communication illustrates the occurrence of a straightforward and selective deprotection procedure, which is typically required to circumvent the occurrence of acidic hydrolysis of the protein backbone. The results hold promise for a large range of biomedical applications in which the presence of primary amines is essential for preserving the biological activity. <boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pghxn0ntg5" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>