NDLI: Synthesis of N-tert.-butoxycarbonyl(α-phenyl)aminomethylphenoxyacetic acid for use as a handle in solid-phase synthesis of peptide α-carboxamides

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Synthesis of N-tert.-butoxycarbonyl(α-phenyl)aminomethylphenoxyacetic acid for use as a handle in solid-phase synthesis of peptide α-carboxamides

Content Provider	Scilit
Author	Gaehde, Stephan A. Matsueda, Gary R.
Copyright Year	2009
Description	Journal: International journal of peptide and protein research N-tert.-butoxycarbonyl-aminomethyl( alpha-phenyl)phenoxyacetic acid was synthesized and found to be suitable for use as a handle in the solid-phase synthesis of peptide alpha-carboxamides. This handle was prepared with an 82% yield when N-tert.-butoxycarbonyl-( rho-hydroxy)benzhydrylamine was treated with excess sodium iodoacetate under alkaline conditions. In stability studies the linkage between the C-terminal amino acid and the handle was found to be resistant to acidolysis in 50% TFA/CH2Cl2 (less than 1% loss after 10h). Upon treatment for 30 min with HF:anisole(9:1) at 0 degrees, 92% cleavage of glycinamide from Gly-handle-resin was obtained. In a test synthesis of a peptide alpha-carboxamide, pyroglutamylhistidylprolinamide was synthesized in 83% yield. Two other handles, tert.-butoxycarbonyl-aminomethylphenoxyacetic acid and N-tert.-butoxycarbonyl-aminomethylphenyloxymethylphenoxyacetic acid, were also synthesized but found to be unsuitable for carboxamide synthesis under the same conditions of solid-phase synthesis.
Related Links	http://onlinelibrary.wiley.com/doi/10.1111/j.1399-3011.1981.tb03006.x/pdf
Ending Page	458
Page Count	8
Starting Page	451
ISSN	03678377
DOI	10.1111/j.1399-3011.1981.tb03006.x
Journal	International journal of peptide and protein research
Issue Number	5
Volume Number	18
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 Boc‐aminomethyl(α‐phenyl)phenoxyacetic Acid As Α‐carboxamide Handle Internal Reference Amino Acids for Evaluation of Carboxamide Synthesis Liquid Hf Cleavage Peptide Α‐carboxamide Synthesis Solid‐phase Peptide Synthesis Stability Against Tfa Acidolysis Thyrotropin‐releasing Hormone Synthesis
Content Type	Text
Resource Type	Article
Subject	Biochemistry

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