Partial transfer of enantioselective chiralities from α-methylated amino acids, known to be of meteoritic origin, into normal amino acids
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Acknowledgments
We thank Dr. Jason Chruma and Dr. Jiaming Yan for some preliminary work and helpful suggestions, and the NSF and NIH for financial support.
References and notes (20)
- et al.
Geochim. Cosmochim. Acta
(2000) - et al.
Geochim. Cosmochim. Acta
(2003) - et al.
Nature
(1982) - et al.
Geochim. Cosmochim. Acta
(2004) - et al.
- et al.
Analyst
(2005) - et al.
Science
(1997) - et al.
Angew. Chem., Int. Ed.
(1998)et al.Acc. Chem. Res.
(2000) Cell. Mol. Life Sci.
(2001)- et al.
Biosystems
(1987)
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Ronald C.D. Breslow (1931–2017): A career in review
2021, Bioorganic ChemistryCitation Excerpt :Combined with a pyridoxamine/pyridoxal small molecule cofactor (vide supra),[330] these systems were able to dramatically accelerate the transamination of ketoacids to amino acids. As a natural continuation of his research in transamination reactions, Breslow developed a prebiotically relevant transamination reaction,[547] in which an excess of a homochiral, C-α-methyl amino acid (α-methyl valine) found on meteorites was combined with an achiral ketoacid, 3-phenylpropanoic acid, to generate phenylalanine with up to 9.5% ee. The proposed reaction mechanism, which occurs via a decarboxylative transamination reaction (Fig. 44), relies on the chiral C-α-methyl amino acid 68a to act both as a source of nitrogen and as a chiral proton source, via its zwitterionic, ammonium-containing state.
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