- Α-substd. provitamin optically active production of phosphorus
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PROBLEM TO BE SOLVED: To provide an industrial method practically suitable for producing an optically active α-substituted prolines with short process and mild conditions.SOLUTION: A method of producing an optically active α-substituted prolines (6) includes (d) a step of obtaining an optically active N, α-substituted prolines (5) by hydrolysis of an optically active N, α-substituted proline amides (4), and (e) a step of obtaining an optically active α-substituted prolines (6) by eliminating the optically active N, and a protective group Rof the α-substituted prolines (5).
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- METHOD FOR PRODUCING OPTICALLY ACTIVE ALPHA-SUBSTITUTED PROLINE
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The present invention aims to provide an industrial method practically suitable for producing optically active α-substituted prolines from an acyclic ketone compound by a small number of steps under mild conditions. The present invention relates to a production method of an optically active α-substituted proline (4) and/or an optically active α-substituted prolinamide (5), including (a) reacting an acyclic ketone compound (1) with at least one selected from ammonia, an ammonium salt, primary amine and a salt of primary amine, and a cyanating agent to give a cyclic nitrogen-containing compound (2), (b) hydrating the cyclic nitrogen-containing compound (2) to give an α-substituted prolinamide (3), and (c) resolving the α-substituted prolinamide (3) by one or more of (d) enzymatical hydrolysis, (e) resolution by diastereomeric salt formation, and (f) separation by column chromatography.
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- Is the backbone conformation of Cα-methyl proline restricted to a single region?
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Cα-Methyl-L-proline, or L(αMe)Pro, is probably the most conformational constrained α-amino acid. In particular, its ω and o torsion angles are restricted to about 180 and -60°, respectively, and only three ranges of values are theoretically ava
- De Poli, Matteo,Moretto, Alessandro,Crisma, Marco,Peggion, Cristina,Formaggio, Fernando,Kaptein, Bernard,Broxterman, Quirinus B.,Toniolo, Claudio
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experimental part
p. 8015 - 8025
(2010/03/31)
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