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Designing the Molybdopterin Core through Regioselective Coupling of Building Blocks
Author(s) -
Pimkov Igor V.,
SerliMitasev Barbara,
Peterson Antoinette A.,
Ratvasky Stephen C.,
Hammann Bernd,
Basu Partha
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502845
Subject(s) - moiety , pterin , regioselectivity , chemistry , pyran , quinoxaline , stereochemistry , molecule , chirality (physics) , combinatorial chemistry , cofactor , organic chemistry , catalysis , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , enzyme , quark
Molybdopterin is an essential cofactor for all forms of life. The cofactor is composed of a pterin moiety appended to a dithiolene‐functionalized pyran ring, and through the dithiolene moiety it binds metal ions. Different synthetic strategies for dithiolene‐functionalized pyran precursors that have been designed and synthesized are discussed. These precursors also harbor 1,2‐diketone or osone functionality that has been condensed with 1,2‐diaminobenzene or other heterocycles resulting in several quinoxaline or pterin derivatives. Use of additives improves the regioselectivity of the complexes. The molecules have been characterized by 1 H and 13 C NMR and IR spectroscopies, as well as by mass spectrometry. In addition, several compounds have been crystallographically characterized. The geometries of the synthesized molecules are more planar than the geometry of the cofactor found in proteins.