Method for producing monatin

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07396941

ABSTRACT:
By simultaneously carrying out an isomerization reaction at position 2 of monatin in different configurations at positions 2 and 4 in the presence of an aldehyde under a condition of pH 4 to 11 in a mixture solvent of water and an organic solvent, and the crystallization of monatin in the same configurations at positions 2 and 4 or a salt thereof, monatin useful as a sweetener, particularly optically active monatin can efficiently be produced.

REFERENCES:
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patent: 2005/0020508 (2005-01-01), Amino et al.
patent: 2005/0137246 (2005-06-01), Amino et al.
patent: 2005/0272939 (2005-12-01), Amino et al.
patent: 2004-222657 (2004-08-01), None
patent: 03/059865 (2003-07-01), None
Jerry March, Advanced Organic Chemistry, 4thedition, 1992, p. 896-7.
Ebbers et al. Tetrahedron, 1997, vol. 53, 28, p. 9417-9476, (disclosed in IDS).
Nakamura et al., Letters, 2000, vol. 2, 19, p. 2967-70, (disclosed in IDS).
Nakamura, Kozo, et al., “Total Synthesis of Montain,” Letters, vol. 2, No. 19, Jun. 23, 2000, pp. 2967-2970.
Holzapfel, C. W., “A Simple Cycloaddition Approach to A Racemate of the Natural Sweetner Monatin,” Synthetic Communications, vol. 24, No. 22, 1994, pp. 3197-3211.
Ebbers, E. J., et al., “Controlled Racemization of Optically Active Organic Compounds: Prospects for Asymmetric Transformation,” Tetrahedron, vol. 53, No. 28, 1997, pp. 9417-9476.
De Jesus Oliveria, D., et al., “Diastereoselective Formation Of A Quaternary Center In A Pyroglutamate Derivative. Formal Syntheis Of Monatin,” Tetrahedron Letters, vol. 42, 2001, pp. 6793-6796.
U.S. Appl. No. 11/627,700, filed Jan. 26, 2007, Amino, et al.
U.S. Appl. No. 11/505,997, filed Aug. 18, 2006, Mori, et al.
Yamada, S., et al., “Method for the Racemization of Optically Active Amino Acids,” J. Org. Chem., vol. 48, No. 6, 1983, pp. 843-846.

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