Ketoreductases in the synthesis of valuable chiral intermediates: Application in the synthesis of α-hydroxy β-amino and β-hydroxy γ-amino acids

Tetrahedron

Volumn 60, Issue 3, 2004, Pages 663-669

  Kambourakis, Spiros ^a   Rozzell, J David ^a  

^a BioCatalytics Inc ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINOALCOHOL; KETONE; NICOTINAMIDE; OXIDOREDUCTASE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CHIRAL CHROMATOGRAPHY; CURTIUS REARRANGEMENT; DIASTEREOISOMER; DRUG SYNTHESIS; ENZYME SYNTHESIS; HYDROLYSIS; METHODOLOGY; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0346964410     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.109     Document Type: Article

References (23)

1. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
2. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
3. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
4. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
5. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
6. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
7. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
8. Some representative publications: (a) Leanna M.R., DeMattei J.A., Li W., Nichols P.J., Rasmussen M., Morton E. Org. Lett. 2:2000;3627 (b) Nicolau K.C., Dai W.M., Guy R.K. Angew. Chem., Int. Ed. Engl. 33:1994;15 (c) Liang B., Richard D.J., Portonovo P.S., Joullie M.M. J. Am. Chem. Soc. 123:2001;4469 (d) Rich D.H., Sun E.T.O. J. Med. Chem. 23:1980;27 (e) Li W.R., Ewing W.R., Harris B.D., Joullie M.M. J. Am. Chem. Soc. 112:1990;7659 (f) Marciniszyn J. Jr., Hartsuck J.A., Tang J. J. Biol. Chem. 251:1976;7088 (g) Jouin P., Poncet J., Dufour M.N., Pantaloni A., Castro B. J. Org. Chem. 54:1989;617 (h) Sun C.I., Chen C.H., Kashiwada Y., Wu J.H., Wang H.K., Lee K.H. J. Med. Chem. 45: 2002;4275 (i) Hom R.K., Fang L.Y., Mamo S., Tung J.S., Guinn A.C., Walker D.E., Davis D.L., Gailunas A.F., Thorsett E.D., Sinha S., Knops J.E., Jewett N.E., Anderson J.P., Varghese J. J. Med. Chem. 46:2003;1799.
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