- The combination of hydroformylation and biocatalysis for the large-scale synthesis of (S)-allysine ethylene acetal
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The compound, (S)-2-amino-5-[1,3]dioxolan-2-yl-pentanoic acid [(S)-allysine ethylene acetal], is a key intermediate in a number of angiotension-I converting enzyme (ACE) and neutral endopeptidase (NEP) inhibitors currently in clinical trials. Through a co
- Cobley, Christopher J.,Lloyd, Michael C.,Simmonds, Shaun,Hanson, Christopher H.,Peng, Wei Jun
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experimental part
p. 284 - 290
(2011/10/02)
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- Process for producing L-allysine acetals
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The present invention has for its object to provide a method for producing an L-allysine acetal which involves a fewer steps and is efficient. This invention relates to method for producing an L-allysine acetal which comprises; converting a D,L-allysine acetal of the following general formula (1) (wherein R1and R2are the same or different, and each of them represents an alkyl group having 1 to 8 carbon atoms, or they combinedly form a ring and represent an alkylene group having 2 to 8 carbon atoms) to a mixture of a 2-oxo-6,6-dialkoxyhexanoic acid of the following general formula (2) (wherein R1and R2are as defined above) and an L-allysine acetal of the following general formula (3) (wherein R1and R2are as defined above) by reacting in the presence of an enzyme capable of stereoselective oxidative deamination of D-amino acids and; isolating said L-allysine acetal after said converting.
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- Method for producing L-Allysine acetal
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A method for producing L-allysine acetal represented by general formula (II), comprising reacting D,L-allysinamide acetal represented by general formula (I) with cells of microorganism or treated cell product having an activity of stereoselectively hydrolyzing L-allysinamide acetal, wherein R1and R2, which may be the same or different, each independently represent a lower alkyl group, or R1and R2are combined to form an alkylene group represented by [CH2]n, and n is 2 to 3. D,L-allysinamide acetal represented by general formula (I) is also in the scope of the invention. According to the present invention, L-allysine acetal useful as a raw material for medicine can be produced in a smaller number of steps at low costs.
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