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Journal Article

Synthesis of nucleopeptides by employing an enzyme-labile urethane protecting group

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Jeyaraj,  Duraiswamy A.
Max Planck Institute of Molecular Physiology, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons98719

Prinz,  Heino
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Jeyaraj, D. A., Prinz, H., & Waldmann, H. (2002). Synthesis of nucleopeptides by employing an enzyme-labile urethane protecting group. Chemistry - A European Journal, 8(8): 1, pp. 1879-1887. Retrieved from http://dx.doi.org/10.1002/1521-3765(20020415)8:8<1879:AID-CHEM1879>3.0.CO;2-5.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-0E93-2
Abstract
Nucleoproteins are naturally occurring biopolymers in which the hydroxy group of a serine, a threonine, or a tyrosine moiety is linked through a phosphodiester group to the 3'- or 5'-end of a nucleic acid. For the study of the biological phenomena in which nucleo-proteins are involved, for example, viral replication, nucleopeptides embodying the characteristic linkage between the peptide chain and the oligonucleotide may serve as powerful tools. However, as a result of the multifunctionality and the pronounced acid and base lability of nucleopeptides, their synthesis requires the application of a variety of orthogonally stable blocking groups, which can be removed under the mildest conditions. We have developed a new mild enzymatic deprotection method, that is, the penicillin G acylase-catalyzed hydrolysis of the N- phenylacetoxybenzyloxycarbony (PhAcOZ) group, for the synthesis of nucleopeptides. We demonstrate the wide applicability of this method by coupling the N-terminally deprotected nucleopeptides 31 a-c with PhAcOZ-protected amino acids and subsequent removal of the N-PhAcOZ group from fully protected nucleotetrapeptides 32a,b with penicillin G acylase. The reaction conditions are very mild (pH 6.8) so that no undesired side reaction such as cleavage of the nucleotide bond or beta- elimination of the nucleotide was observed.