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Molecules 2011, 16(4), 3232-3251; doi:10.3390/molecules16043232

Selenol Protecting Groups in Organic Chemistry: Special Emphasis on Selenocysteine Se-Protection in Solid Phase Peptide Synthesis

University of Vermont, 116 Cook Bldg, 82 University Place, Burlington, VT 05405, USA
Received: 1 March 2011 / Revised: 3 April 2011 / Accepted: 12 April 2011 / Published: 18 April 2011
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
Download PDF [308 KB, 18 June 2014; original version 18 June 2014]


The appearance of selenium in organic synthesis is relatively rare, and thus examples in the literature pertaining to the masking of its considerable reactivity are similarly uncommon. Greene's Protecting Groups in Organic Synthesis, the standard reference for the state of the art in this arena, offers no entries for selenium protective methodology, in stark comparison to its mention of the great variety of protecting groups germane to its chalcogen cousin sulfur. This scarcity of Se-protection methods makes it no less interesting and pertinent toward the construction of selenium-containing organic systems which do indeed require the iterative blocking and de-blocking of selenol functionalities. A selenium-containing system which is especially relevant is selenocysteine, as its use in Solid Phase Peptide Synthesis requires extensive protection of its selenol side chain. This review will attempt to summarize the current state of understanding with regard to selenium protection protocol in organic synthesis. Moreover, it will provide a special emphasis on selenocysteine side chain protection, comprising both the breadth of functionality used for this purpose as well as methods of deprotection.
Keywords: selenium; selenocysteine; protecting group; protection selenium; selenocysteine; protecting group; protection
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Flemer Jr., S. Selenol Protecting Groups in Organic Chemistry: Special Emphasis on Selenocysteine Se-Protection in Solid Phase Peptide Synthesis. Molecules 2011, 16, 3232-3251.

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