Oxime-Based Carbonates as Useful Reagents for Both N-Protection and Peptide Coupling 英文参考文献.docVIP

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Oxime-Based Carbonates as Useful Reagents for Both N-Protection and Peptide Coupling 英文参考文献.doc

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Oxime-Based Carbonates as Useful Reagents for Both N-Protection and Peptide Coupling 英文参考文献

Molecules 2012, 17, 14361-14376; doi:10.3390/molecules171214361 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Oxime-Based Carbonates as Useful Reagents for Both N-Protection and Peptide Coupling Yahya El-Sayed Jad 1, Sherine N. Khattab 1, Ayman El-Faham 1,2,3,* and Fernando Albericio 3,4,5,6, * 1 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, 21321 Alexandria, Egypt 2 Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 11451 Riyadh, Saudi Arabia 3 Department of Chemistry and Molecular Pharmacology, Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain 4 CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain 5 Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Spain 6 School of Chemistry, University of KwaZulu-Natal, 4041 Durban, South Africa * Authors to whom correspondence should be addressed; E-Mails: aymanel_faham@ (A.E.-F.); albericio@ (F.A.); Tel.: +20-122-3140-924 (A.E.-F.); Fax: +20-3-5771-399 (A.E.-F.); Tel./Fax: +34-93-4037-126 (F.A.). Received: 22 October 2012; in revised form: 23 November 2012 / Accepted: 30 November 2012 / Published: 5 December 2012 Abstract: We have demonstrated that oxime-based mixed carbonates are very effective reagents for both N-protection and peptide coupling. Keywords: oxime; additives; N-protection; activation; coupling; peptide 1. Introduction Peptides are increasingly gaining recognition as potential bioactive ingredients in the pharmaceutical industry [1–3]. Peptide synthesis depends on the strategies used for protecting the α-amino group and for activating the carboxylic acid group prior to peptide coupling. The two main classes [4–6] of carboxylic acid group activation methods are: (i) those that require in situ activ