Document Detail

Synthesis and characterisation of hetero-bimetallic organometallic phenylalanine and PNA monomer derivatives.
MedLine Citation:
PMID:  19662308     Owner:  NLM     Status:  MEDLINE    
The rational, sequential synthesis of two hetero-bimetallic derivatives of the amino acid phenylalanine and one thymine (T) peptide nucleic acid (PNA) monomer is reported. Ferrocene carboxylic acid and (eta-ethene)bis(triphenylphosphine)platinum(0) were successfully reacted with propargylamide amino acid (1a and 1b) or a T PNA monomer derivative (6) to give the expected three bimetallic compounds 4a, 4b and 9 in good yield. An enzymatic route using cross-linked enzyme crystals (CLEC) of subtilopeptidase A in organic solvents gave the ferrocene carboxylate phenylalanine propargylamide precursor (Fc-CO-Phe-NH-CH(2)-CCH, 3a) in comparable yield and purity to the traditional deprotection-peptide coupling sequence. (31)P NMR spectra of these bioorganometallics showed two doublets with (195)Pt satellites corresponding to two chemically different (31)P atoms. Interestingly, in the case of the T PNA monomer derivative 9, these signals were also doubled in a 60 : 40 ratio as a consequence of the existence of two slowly interconverting isomers in solution. Furthermore, the single-crystal X-ray structures of 3a and the hetero-bimetallic phenylalanine derivative 4b were determined, showing the presence of the two organometallics moieties separated by ca. 8.5 A in 4b as well as illustrating the stability of such compounds.
Gilles Gasser; Oliver Brosch; Alexandra Ewers; Thomas Weyhermüller; Nils Metzler-Nolte
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-02-09
Journal Detail:
Title:  Dalton transactions (Cambridge, England : 2003)     Volume:  -     ISSN:  1477-9226     ISO Abbreviation:  Dalton Trans     Publication Date:  2009 Jun 
Date Detail:
Created Date:  2009-08-07     Completed Date:  2009-09-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101176026     Medline TA:  Dalton Trans     Country:  England    
Other Details:
Languages:  eng     Pagination:  4310-7     Citation Subset:  IM    
Lehrstuhl für Anorganische Chemie I-Bioanorganische Chemie, Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Bochum, Germany.
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MeSH Terms
Alkynes / chemical synthesis,  chemistry
Crystallography, X-Ray
Ferrous Compounds / chemical synthesis,  chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Organometallic Compounds / chemical synthesis*,  chemistry
Peptide Nucleic Acids / chemical synthesis*,  chemistry
Phenylalanine / chemical synthesis*,  chemistry
Phosphines / chemical synthesis,  chemistry
Platinum / chemistry*
Thymine / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Alkynes; 0/Ferrous Compounds; 0/Organometallic Compounds; 0/Peptide Nucleic Acids; 0/Phosphines; 102-54-5/ferrocene; 63-91-2/Phenylalanine; 65-71-4/Thymine; 7440-06-4/Platinum; 7803-51-2/phosphine

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