Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine.

@article{Shiraiwa2002SynthesisOO,
  title={Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine.},
  author={Tadashi Shiraiwa and Kazuo Nakagawa and Norito Kanemoto and Tomohiro Kinda and Hiroki Yamamoto},
  journal={Chemical \& pharmaceutical bulletin},
  year={2002},
  volume={50 8},
  pages={
          1081-5
        }
}
In order to synthesize four stereoisomers of cystathionine (CYT), D- and L-homocysteines (D- and L-Hcy) were synthesized from methionine (Met) by a facile procedure. L-Met was reacted with dichloroacetic acid in concentrated hydrochloric acid under reflux to give (4S)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [(4S)-TDC.HCl]. L-Hcy was obtained by treatment of (4S)-TDC.HCl with hydroxylamine. D-Hcy was also synthesized from D-Met via (4R)-TDC.HCl intermediate. The obtained D- and L-Hcy… Expand
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DL-Homocysteine [DL-Hcy] from (RS)-homocysteine thiolactone hydrochloride [(RS)-HTL·HCl] was subjected to reaction with formaldehyde in acetic acid to give (RS)-1,3-thiazane-4-carboxylic acidExpand
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Stereospecific syntheses of cycloserine (D-4-amino-3-isoxazolidinone) are described. The same synthetic methods lead to some 5-substituted 4-amino-3-isoxazolidinones. The stereochemical relationshipExpand
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