General base-guanidinium cooperation in bifunctional artificial phosphodiesterases

Riccardo Salvio; Roberta Cacciapaglia; Luigi Mandolini

doi:10.1021/jo2004007

General base-guanidinium cooperation in bifunctional artificial phosphodiesterases

J Org Chem. 2011 Jul 1;76(13):5438-43. doi: 10.1021/jo2004007. Epub 2011 Jun 7.

Authors

Riccardo Salvio¹, Roberta Cacciapaglia, Luigi Mandolini

Affiliation

¹ Dipartimento di Chimica and IMC-CNR Sezione Meccanismi di Reazione, Università La Sapienza, P.le Aldo Moro 5, 00185 Roma, Italy.

PMID: 21612212
DOI: 10.1021/jo2004007

Abstract

Artificial phosphodiesterases that combine a guanidinium unit with a general base connected by a m-xylylene linker catalyze the transesterification of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate (HPNP). The bifunctional catalysts presented in this work show varying extents of cooperation between catalytic units and a rate enhancement of 4 × 10(4) in the most favorable case.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biocatalysis
Copper / chemistry
Guanidine / chemistry*
Hydrogen-Ion Concentration
Molecular Structure
Organometallic Compounds / chemistry
Phosphoric Diester Hydrolases / chemistry
Phosphoric Diester Hydrolases / metabolism*
Ribonucleotides / chemistry
Ribonucleotides / metabolism
Stereoisomerism
Xylenes / chemistry

Substances

Organometallic Compounds
Ribonucleotides
Xylenes
Copper
Phosphoric Diester Hydrolases
Guanidine
3-xylene