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  Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis

Völkert, M., Koul, S., Müller, G. H., Lehnig, M., & Waldmann, H. (2002). Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis. Journal of Organic Chemistry, 67(20): 1, pp. 6902-6910. Retrieved from http://dx.doi.org/10.1021/jo0259966.

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Genre: Journal Article
Alternative Title : J. Org. Chem.

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 Creators:
Völkert, Martin1, Author
Koul, Surrinder, Author
Müller, Gernot H., Author
Lehnig, Manfred, Author
Waldmann, Herbert2, Author           
Affiliations:
1Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753286              
2Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society, ou_1753290              

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 Abstract: The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.181.1) 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 methionine residues was not observed. These features make the methodology suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism.

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Language(s): eng - English
 Dates: 2002-10-01
 Publication Status: Issued
 Pages: -
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 13693
URI: http://dx.doi.org/10.1021/jo0259966
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Title: Journal of Organic Chemistry
  Alternative Title : J. Org. Chem.
Source Genre: Journal
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Publ. Info: -
Pages: - Volume / Issue: 67 (20) Sequence Number: 1 Start / End Page: 6902 - 6910 Identifier: -