L-Alamne

The method described here illustrates the transformation of optically active 2-chlorocarboxylic acids, which are readily available from 2-amino acids,2 via 2-chloroalkan-l-ols to alkyloxiranes with inversion of configuration at the stereocenter. Thus (R)-methyloxirane is prepared from (S)-alamne, (R)-isopropyloxirane from (S)-valine, (R)-isobutyl0x1 rane from... 

A compound with only one asymmetric center, L(-f)-alamne was studied by Kay et al. (1959). Substitution at the a-carbon in the crystalline material occurs with complete retention of configuration within the limits of error of the experiment. Substitution at the )3-carbon results in at least 85% retention, but possibly all of the events occur with retention. Studies on L(- -)-alanine in solution gave similar results. 

Ohwada et al. [54] synthesized a derivative of the salty peptide V ,V -dicarbobenzoxy-L-omithyl- 3-alamne benzyl ester (Zz-Om(Z)-3-Ala-OBzl) in 1,1,1-trichloroethane using PEG-papain (Fig. 5). 

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