e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis

…, GH Müller, M Lehnig, H Waldmann

Index: Voelkert, Martin; Koul, Surrinder; Mueller, Gernot H.; Lehnig, Manfred; Waldmann, Herbert Journal of Organic Chemistry, 2002 , vol. 67, # 20 p. 6902 - 6910

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Citation Number: 21

Abstract

The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14. 18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo-and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive ...

Z-Leu-OH Structure

Phenylhydrazine hydrochloride Structure

Phenylhydrazine...

~21%

L-Leucine,N-[(phenylmethoxy)carbonyl]-, 2-phenylhydrazide Structure

L-Leucine,N-[(p...

Z-Ala-NHNHPh Structure

~71%

N-Carbobenzyloxy-L-alanine Structure

N-Carbobenzylox...

N/A Structure

~9%

Fmoc-Phe-Phe-OH Structure

Fmoc-Phe-Phe-OH

Z-Gly-NHNHPh Structure

~93%

Z-Gly-OH Structure

Boc-Phe-Phe-NHNHPh Structure

Boc-Phe-Phe-NHNHPh

~26%

Boc-Phe-Phe-OH Structure

N/A Structure

~%

BOC-LEU-PRO-OH Structure

Boc-Leu-NHNHPh Structure

~%

BOC-LEU-PRO-OH Structure

Boc-Leu-NHNHPh Structure

~86%

Boc-Leu-OH.H2O Structure

Z-Ala-Pro-NHNHPh Structure

Z-Ala-Pro-NHNHPh

~66%

Z-ALA-PRO-OH Structure

N-Carbobenzyloxy-L-alanine Structure

N-Carbobenzylox...

~%

Z-ALA-PRO-OH Structure

Boc-L-Proline Structure

~%

Z-ALA-PRO-OH Structure

Z-Ala-NHNHPh Structure

~%

Z-ALA-PRO-OH Structure

Fmoc-Pro-OH Structure

~%

Z-ALA-PRO-OH Structure

H-Pro-NHNHPh Structure

~%

Z-ALA-PRO-OH Structure

(S)-tert-butyl 2-(2-phenylhydrazinecarbonyl)pyrrolidine-1-carboxylate Structure

(S)-tert-butyl ...

~%

Z-ALA-PRO-OH Structure

Fmoc-Pro-NHNHPh Structure

Fmoc-Pro-NHNHPh

~%

Z-ALA-PRO-OH Structure

N-tert-Butyloxycarbonyl-phenylalanin-phenylhydrazide Structure

N-tert-Butyloxy...

~63%

Boc-L-phenylalanine Structure

Boc-L-phenylalanine

Boc-Gly-Leu-NHNHPh Structure

Boc-Gly-Leu-NHNHPh

~%

N-Boc-glycyl-L-leucine Structure

N-Boc-glycyl-L-...

Boc-Gly-OH Structure

~%

N-Boc-glycyl-L-leucine Structure

N-Boc-glycyl-L-...

Boc-Gly-NHNHPh Structure

~%

N-Boc-glycyl-L-leucine Structure

N-Boc-glycyl-L-...

N/A Structure

~98%

Boc-L-Valine Structure

Boc-Trp-NHNHPh Structure

~44%

N-[(tert-Butoxy)carbonyl]-L-tryptophan Structure

N-[(tert-Butoxy...

Boc-Gly-NHNHPh Structure

~87%

Boc-Gly-OH Structure

Papain-catalyzed synthesis of phenylhydrazides of N-acylamin...

[Cerovsky, Vaclav; Jost, Karel Collection of Czechoslovak Chemical Communications, 1984 , vol. 49, # 11 p. 2557 - 2561]