Amino-acids condensations in the preparation of N ...[Int J Pept Protein Res. 1983]

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1: Int J Pept Protein Res. 1983 Jul;22(1):125-8.Links

Amino-acids condensations in the preparation of N alpha-9-fluorenylmethyloxycarbonylamino-acids with 9-fluorenylmethylchloroformate.

Tessier M, Albericio F, Pedroso E, Grandas A, Eritja R, Giralt E, Granier C, Van Rietschoten J.

Synthesis of N alpha-9-fluorenylmethyloxycarbonyl (Fmoc) amino-acids by reaction of free amino-acids (glycine and alanine) with 9-fluorenylmethylchloroformate leads to formation of small amounts of Fmoc-dipeptide which are difficult to eliminate by crystallization. The alternative way to prepare Fmoc-amino-acids by reacting the Fmoc-chloride first with sodium azide and then with the free amino-acid eliminates this side reaction, at least for glycine and alanine.

PMID: 6885246 [PubMed - indexed for MEDLINE]

Preparation, isolation, and characterization of Nalpha-Fmoc-peptide isocyanates: solution synthesis of oligo-alpha-peptidyl ureas.
J Org Chem. 2006 Sep 29; 71(20):7697-705.

[J Org Chem. 2006]
Application of N,N-dimethylformamide dineopentyl acetal for efficient anchoring of N alpha-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis.
Int J Pept Protein Res. 1984 Apr; 23(4):342-9.

[Int J Pept Protein Res. 1984]
Solid-phase peptide synthesis of somatostatin using mild base cleavage of N alpha-9-fluorenylmethyloxycarbonylamino acids.
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[Int J Pept Protein Res. 1980]
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[Methods Mol Biol. 2006]
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Biopolymers. 2000; 55(2):123-39.

[Biopolymers. 2000]
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Amino-acids condensations in the preparation of N alpha-9-fluorenylmethyloxycarbonylamino-acids with 9-fluorenylmethylchloroformate.

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