Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids

Stephan J. Zuend, Matthew P. Coughlin, Mathieu P. Lalonde and Eric N. Jacobsen ()
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Stephan J. Zuend: Harvard University, Cambridge, Massachusetts 02138, USA
Matthew P. Coughlin: Harvard University, Cambridge, Massachusetts 02138, USA
Mathieu P. Lalonde: Harvard University, Cambridge, Massachusetts 02138, USA
Eric N. Jacobsen: Harvard University, Cambridge, Massachusetts 02138, USA

Nature, 2009, vol. 461, issue 7266, 968-970

Abstract: Alpha-amino acids on tap A team from Harvard's Department of Chemistry and Chemical Biology reports the culmination of a long-term project, the development of a practical and adaptable method for synthesizing α-amino acids, the building blocks of proteins. The synthesis is based on an organic chemistry classic, the Strecker reaction. A simple chiral amido-thiourea molecule is used to catalyse the addition of hydrogen cyanide to imines with high selectivity and under conditions that allow its use on large scales. New and unusual amino acids can be synthesized, with broad application to a wide range of fields including medicinal chemistry, protein science and material science.

Date: 2009
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DOI: 10.1038/nature08484

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