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  Home > JCE Print > Journal of Chemical Education > Issues > 2002  > May  >
Chemical Education Today
Letters
On the Stereochemistry of 'Natural' a-Amino Acids (re J. Chem. Educ. 2000, 77, 48-49)
Giovanni Lentini
Dipartimento Farmaco-Chimico, Facoltà di Farmacia, 70125 Bari, Italy
Cover
May 2002
Vol. 79 No. 5
p. 558
Full Text
In the first issue of 2000, I enjoyed the intriguing article by S. H. Leung on the common names of naturally occurring and synthetic compounds (J. Chem. Educ. 2000, 77, 48-49). Despite the care the author took in retrieving and reporting the derivation for a lot of names, in my opinion a major correction should be introduced in Table 1, where the systematic names for amino acids are given. Assuming that this list concerns "natural" amino acids (they are referred to as "biologically important" in note a) they all belong to the l steric series, with the obvious exception of glycine. Thus, the correct stereochemical descriptor for the absolute configuration at the α-carbon atom should be (S) for all of them but cysteine (and cystine, of course). In fact, since HSCH2­ has a higher priority than HO2C­, L-cysteine is an exception to the generalization that all natural amino acids have (S) configuration at their α-carbon atom: actually, L-cysteine has (R) configuration.

See the author's reply.

More Information
*  Citation
 Lentini, Giovanni. J. Chem. Educ. 2002 79 558.
*  Keywords
 Amino Acids; Nomenclature / Units / Symbols; Stereochemistry
*  History
 Created:
Last Updated:		 April 1, 2002
March 16, 2005
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