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To enable this MD study, a molecular mechanics force field for ferrocene\u2010bearing peptides was developed and implemented in the CHARMM simulation package, thus extending the usefulness of the package into peptide\u2013bioorganometallic chemistry. Using the automated frequency\u2010matching method (AFMM), optimized intramolecular force\u2010field parameters were generated through quantum chemical reference normal modes. The partial charges for ferrocene were derived by fitting point charges to quantum\u2010chemically computed electrostatic potentials. The force field was tested against experimental X\u2010ray crystal structures of dipeptide derivatives of ferrocene\u20101,1\u2032\u2010dicarboxylic acid. The calculations reproduce accurately the molecular geometries, including the characteristic <jats:italic>C<\/jats:italic><jats:sub>2<\/jats:sub>\u2010symmetrical intramolecular hydrogen\u2010bonding pattern, that were stable over 0.1\u2005\u03bcs MD simulations. The crystal packing properties of ferrocene\u20101\u2010(<jats:sc>D<\/jats:sc>)alanine\u2010(<jats:sc>D<\/jats:sc>)proline\u20101\u2032\u2010(<jats:sc>D<\/jats:sc>)alanine\u2010(<jats:sc>D<\/jats:sc>)proline were also accurately reproduced. The lattice parameters of this crystal were conserved during a 0.1\u2005\u03bcs MD simulation and match the experimental values almost exactly. Simulations of the peptides in dichloromethane are also in good agreement with experimental NMR and circular dichroism (CD) data in solution. The developed force field was used to perform MD simulations on novel, as yet unsynthesized peptide fragments that surround the active site of [Ni\u2013Fe] hydrogenase. The results of this simulation lead us to propose an improved design for synthetic peptide\u2010based hydrogenase models. The presented MD simulation results of metallocenes thereby provide a convincing validation of our proposal to use ferrocene\u2013peptides as minimal enzyme mimics.<\/jats:p>","DOI":"10.1002\/chem.200700358","type":"journal-article","created":{"date-parts":[[2007,8,31]],"date-time":"2007-08-31T09:47:16Z","timestamp":1188553636000},"page":"8139-8152","source":"Crossref","is-referenced-by-count":33,"title":["Force\u2010Field Development and Molecular Dynamics Simulations of Ferrocene\u2013Peptide Conjugates as a Scaffold for Hydrogenase Mimics"],"prefix":"10.1002","volume":"13","author":[{"given":"Xavier","family":"de\u2005Hatten","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zoe","family":"Cournia","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ivan","family":"Huc","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeremy\u2005C.","family":"Smith","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nils","family":"Metzler\u2010Nolte","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2007,9,25]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-4660(199909)74:9<852::AID-JCTB131>3.0.CO;2-T"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/16601"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0038-092X(80)90018-3"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/373580a0"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic0343760"},{"key":"e_1_2_7_6_2","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/B0-08-043748-6\/08138-X","volume-title":"Comprehensive Coordination Chemistry II, Vol. 8","author":"Georgakaki I. 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