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Preparation of protected peptide amides using the Fmoc chemical protocol

Content Provider	Scilit
Author	Story, Sandra C. Aldrich, Jane V.
Copyright Year	2009
Description	Journal: International journal of peptide and protein research Different resins were examined for their potential use in the solid phase synthesis of protected peptide amides using the 9-fluorenylmethoxycarbonyl (Fmoc) chemical protocol. The model protected peptide amide BocTyr-Gly-Gly-Phe-Leu-Arg(Pmc)NH2 (1) was synthesized on both the acid-labile 4-(2',4'-dimethoxyphenyl-Fmoc-aminomethyl)phenoxy resin (Rink amide resin) (2) and on resins containing the base-labile linker 4-hydroxymethylbenzoic acid. Of the resins examined only the methylbenzhydrylamine resin containing the 4-hydroxymethylbenzoic acid linkage, which was cleaved by ammonolysis in isopropanol, gave the model peptide 1 in good overall yield (53% including functionalization). Thus the synthesis of protected peptide amides by solid phase synthesis using Fmoc-protected amino acids with t-butyl-type side chain protecting groups is feasible. The choice of peptide-resin linkage and its cleavage conditions, however, are critical to the success of such syntheses. The potential application of this synthetic strategy to the preparation of novel peptide amides is discussed.
Related Links	http://onlinelibrary.wiley.com/doi/10.1111/j.1399-3011.1992.tb01560.x/pdf
Ending Page	92
Page Count	6
Starting Page	87
ISSN	03678377
DOI	10.1111/j.1399-3011.1992.tb01560.x
Journal	International journal of peptide and protein research
Issue Number	1
Volume Number	39
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2009-01-12
Access Restriction	Open
Subject Keyword	Journal: International journal of peptide and protein research Organic Chemistry Fluorenylmethoxycarbonyl (fmoc) Synthetic Strategy Protected Peptide Amide Resins for Solid Phase Peptide Synthesis 4‐hydroxymethylbenzoic Acid Linker Rink Amide Resin Solid Phase Peptide Synthesis
Content Type	Text
Resource Type	Article
Subject	Biochemistry

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