Model Reactions for Oxidative Phosphorylation: Sulfur Compounds as Carriers of the Phosphoryl Group

✍ Scribed by Dr. Edmund Bäuerlein; Prof. Dr. Theodor Wieland

• Publisher: John Wiley and Sons
• Year: 1971
• Tongue: English
• Weight: 207 KB
• Volume: 10
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.197105211

✦ Synopsis

acryloyl chloride ; 2) by treatment of optically active amino esters and tertiary amines with crosslinked chloromethylated polystyrene ; and 3) by polymerization of optically active acrylic esters and amides.

Resolution was studied in each case with 1-IOmg of doubly labeled racemic mandelic acid on 10-cm columns. With almost all the adsorbents enrichment of one antipode was definitely detectable, at least in the first and last fractions of the eluate. With cinchonine polyacrylate prepared by method (1) it amounted to IS%, the (R)-( -)-antipode being enriched in the first fractions. The separation on ephedrine esters [N-benzylephedrine polyacrylate 30%, (S)-( +)-antipode eluated first] was even more marked and could be further improved if the chiral center were built into a rigid skeleton (Fig. 1).

It is remarkable that the elution profile shows two maxima. By using longer columns of the synthetic adsorbents it is now possible for the first time to resolve racemates quantitatively. Further, the second racemate tested by us, namely, methyl mandelate, is also partly separated into its antipodes on the adsorbents reported above.