Chiral Recognition of α-Amino Acids by an Optically Active (2S,5S,8S,11S)-2,5,8,11-Tetraethyl Cyclen Cobalt(III) Complex

The optically active cobalt(III) complex with chiral cyclen, (2S,5S,8S,11S)-2,5,8,11-tetraethyl-1,4,7,10-tetraazacyclododecane, preferentially binds to d-phenylglycine (d-Phg) or d-t-leucine (d-t-Leu) rather than l-Phg or l-t-Leu, respectively, with 20% de in dimethyl sulfoxide at 293 K. Comparative...

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Bibliographic Details
Published in:Inorganic chemistry 2011-01, Vol.50 (1), p.4-6
Main Authors: Tashiro, Shohei, Ogura, Yasuyo, Tsuboyama, Sei, Tsuboyama, Kaoru, Shionoya, Mitsuhiko
Format: Article
Language:English
Subjects:
Cobalt - chemistry
Coordination Complexes - chemistry
Crystallography, X-Ray
Glycine - analogs & derivatives
Glycine - chemistry
Glycine - metabolism
Heterocyclic Compounds - chemistry
Leucine - chemistry
Leucine - metabolism
Magnetic Resonance Spectroscopy
Models, Molecular
Stereoisomerism
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Summary:The optically active cobalt(III) complex with chiral cyclen, (2S,5S,8S,11S)-2,5,8,11-tetraethyl-1,4,7,10-tetraazacyclododecane, preferentially binds to d-phenylglycine (d-Phg) or d-t-leucine (d-t-Leu) rather than l-Phg or l-t-Leu, respectively, with 20% de in dimethyl sulfoxide at 293 K. Comparative studies on the crystal structures of cobalt(III) complexes with d-Phg and l-Phg revealed that the diastereoselectivity is due to the difference in the steric hindrance that should occur between the amino group of Phg and the ethyl group of cyclen.
ISSN:0020-1669
1520-510X
DOI:10.1021/ic101760k