NDLI: Improved approach for anchoring Nα-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis

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Improved approach for anchoring Nα-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis

Content Provider	Scilit
Author	Albericio, Fernando Barany, George
Copyright Year	2009
Description	Journal: International journal of peptide and protein research Several Fmoc-amino acids have been esterified by use of N,N-dimethylformamide dineopentyl acetal to 2,4,5-trichlorophenyl 3'-(4''-hydroxymethyl-phenoxy)propionate, and the resultant handle derivatives were purified and then quantitatively coupled onto aminomethyl supports. Compared to literature methodology, the present procedure is preferred because: (i) extra steps to selectively protect and liberate the carboxyl of the handle are circumvented; and (ii) the additional methylene group spacer reflecting substitution of a propionyl group for an acetyl group in the handle changes the electronic parameters of the resultant p-alkoxybenzyl ester sufficiently so that the rates of acidolytic cleavage of the anchoring linkage are 2- to 3-fold increased and useful improvements in yields can be achieved.
Related Links	http://onlinelibrary.wiley.com/doi/10.1111/j.1399-3011.1985.tb03182.x/pdf
Ending Page	97
Page Count	6
Starting Page	92
ISSN	03678377
DOI	10.1111/j.1399-3011.1985.tb03182.x
Journal	International journal of peptide and protein research
Issue Number	1
Volume Number	26
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 P‐alkoxybenzyl Esters N,n‐dimethylformamide Dineopentyl Acetal Nα‐9‐fluorenylmethyloxycarbonylamino Acids 2,4,5‐trichlorophenyl 3'‐(4“‐hydroxy‐methylphenoxy)propionate Handle Solid‐phase Peptide Synthesis
Content Type	Text
Resource Type	Article
Subject	Biochemistry

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Application of N,N-dimethylformamide dineopentyl acetal for efficient anchoring of Nα-9-fluorenylmethyloxycarbonylamino-acids as p-alkoxybenzyl esters in solid-phase peptide synthesis

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