Selenol Protecting Groups in Organic Chemistry Special Emphasis on Selenocysteine Se-Protection in Solid Phase Peptide Synthesis 英文参考文献.docVIP

Molecules 2011, 16, 3232-3251; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Selenol Protecting Groups in Organic Chemistry: Special Emphasis on Selenocysteine Se-Protection in Solid Phase Peptide Synthesis Stevenson Flemer Jr. 116 Cook Bldg; 82 University Place; University of Vermont; Burlington, VT 05405, USA; E-Mail: sflemer@; Tel.: +1-802-656-0269; Fax: +1-802-656-8705. Received: 1 March 2011 in revised form: 3 April 2011 / Accepted: 12 April 2011 / Published: 18 April 2011 Abstract: 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. Greenes 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 1. Introduction Selenium is a chalcogen element which, alth