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A Simple Method for Determining the Absolute Configuration of alpha-Amino Acids

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Esteban P. Urriolabeitia

Departamento de Química Inorgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, 50009 Zaragoz, Spain

María Dolores Díaz-de-Villegas

Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-CSIC, 50009 Zaragoz, Spain

J. Chem. Educ., 1999, 76 (1), p 77

DOI: 10.1021/ed076p77

Publication Date (Web): January 1, 1999

Abstract

The reaction of [Pd(dmba)(acac)] (dmba = C₆H₄CH₂NMe₂-2 or 2-[(dimethylamino)methyl]phenyl-C¹,N; acac = C₅H₇O₂ or acetylacetonate) with optically pure α-amino acids (HAa, 1:1 molar ratio) [HAa = S-alanine, S-2-amino butyric acid, R-2-amino butyric acid, (2S,3S)-isoleucine, (2S,3R)-threonine and S-asparagine] in refluxing MeOH results in the formation of the corresponding neutral complexes [Pd(dmba)(Aa)] in good yield. The CD (circular dichroism) spectra of these complexes have been measured. The analysis of the shape of the CD curves reveals that all complexes with the same configuration at C_α display similar CD curves, whereas complexes with opposite configuration at C_α display CD curves that are mirror images. Thus, these complexes could be used as analytical tools in the assignment of absolute configurations of α-amino acids.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Inorganic Chemistry

Keywords (Subject):

Organometallics

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