Resolution of 2-amino-5-thiomethyl pentanoic acid (homomethionine) with aminopeptidase from Pseudomonas Putida or chiral phosphoric acids.
✍ Scribed by B.K Vriesema; H ten Hoeve; H Wynberg; Richard M Kellogg; W.H.J Boesten; E.M Meijer; H.E Schoemaker
- Book ID
- 104218527
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 226 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Both enantiomers of homomethionine have been obtained very readily by either of two newly developed resolution methods. The absolute configuration of homomethionine has been established with the aid of circular dichroic (CD) measurements. Homomethionine (la) is a naturally occurring amino acid that serves apparently as the precursor of the aglycone of sinigrin (2_), found in black mustard seed and horseradish root.' It is a member of a family of homologs, starting with methionine (s), which is the 0 RS(CHZ),CHCOs L a) n=3;R=CHs b) n=l;R=H c) n=2:R=CH3 so@ It@ 1 3' biosynthetic precursor of la. 2 The lengthening of the chain by one methylene unit (lc to la) --involves a complex sequence of reactions that begins with deamination, followed by addition of acetate, decarboxylation, and adjustment of oxidation levels. 3
Homomethionine is also of potential interest as a precursor of various chiral intermediates for synthetic purposes.