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Synthesis and spectroscopic characterization of dimethylgermanium derivatives of dipeptides, crystal structure of dimethylgermanium glycylglycinate and in vivo effects of dimethylgermanium glycylglycinate against murine leukemia P388
Author(s) -
Vornefeld Michael,
Huber Friedo,
Preut Hans,
Brunner Henri
Publication year - 1989
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590030210
Subject(s) - chemistry , triethylamine , in vivo , dipeptide , trigonal bipyramidal molecular geometry , crystal structure , stereochemistry , hydrolysis , aqueous solution , raman spectroscopy , molecule , prodrug , crystallography , peptide , organic chemistry , biochemistry , microbiology and biotechnology , biology , physics , optics
Dimethylgermanium derivatives of dipeptides, Me 2 GeAA (H 2 AA = H 2 glygly, H 2 glyala, H 2 glyval, H 2 glyleu, H 2 glymet) have been obtained by the reaction of Me 2 GeBr 2 with H 2 AA in the presence of triethylamine. The crystal structure of Me 2 Geglygly has been determined by single‐crystal X‐ray diffraction. The dipeptide is tridentately coordinated to germanium, which has a distorted trigonal bipyramidal environment. From infrared and Raman data, analogous molecular structures are inferred for the other dimethylgermanium derivatives of dipeptides. 1 H NMR measurements show that Me 2 Geglygly is completely hydrolyzed in aqueous solution to give H 2 glygly and (Me 2 Geo) x . In vivo tests with Me 2 Geglygly showed no toxic or antitumor activity against murine leukemia P388.