An efficient synthesis of chiral amino acid and peptide alkylamides via CLEC-subtilisin catalyzed coupling and in situ resolution

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5317-5320

  Wang, Yi Fong ^a   Yakovlevsky, Kirill ^a   Margolin, Alexey L ^a  

^a Altus Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PEPTIDE DERIVATIVE; SUBTILISIN;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0030598063     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01119-7     Document Type: Article

References (31)

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16. 8. The N-hydroxy imides are not commercially available.
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18. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
19. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
20. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
21. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
22. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
23. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
24. 10. de Zoete, M.C.; Ouwehand, A.A.; van Rantwijk, F.; Sheldon, R.A. Rec. Travaux Chim. Pays-Bas, 1995, 114, 171-174. Quiros, M.; Sanchez, V.M.; Brieva, R.; Rebolledo, F.; Gotor, V., Tetrahedron: Asymmetry, 1993, 4, 1105. Puertas, S.; Rebolledo, F.; Gotor, V., Tetrahedron, 1995, 51, 1495. Gotor, V.; Menendez, E.; Mouloungui, Z.; Gaset, A., J. Chem. Soc., Perkin Trans. I, 1993, 2453. Garcia, J.M.; Rebolledo, F.; Gotor, V., Tetrahedron, 1994, 50, 6935. Kitaguchi, H.; Fitzpatrick, P.A.; Huber, J.E.; Klibanov, A.M., J. Am. Chem. Soc., 1989, 111, 3094. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry, 1995, 6, 2797-2802.
25. 11. St. Clair, N.L.; Navia, M.A. J. Am. Chem. Soc. 1992, 114, 7314. Persichetti, R.A.; St. Clair, N.L.; Griffith, J.P.; Navia, M.A.; Margolin, A.L. J. Am. Chem. Soc. 1995, 117, 2732. Lalonde, J.J., Govardhan, C.P., Khalaf, N.K., Martinez, O.G., Visuri, K.J., Margolin, A.M., J. Am. Chem. Soc., 1995, 117, 6845.
26. 11. St. Clair, N.L.; Navia, M.A. J. Am. Chem. Soc. 1992, 114, 7314. Persichetti, R.A.; St. Clair, N.L.; Griffith, J.P.; Navia, M.A.; Margolin, A.L. J. Am. Chem. Soc. 1995, 117, 2732. Lalonde, J.J., Govardhan, C.P., Khalaf, N.K., Martinez, O.G., Visuri, K.J., Margolin, A.M., J. Am. Chem. Soc., 1995, 117, 6845.
27. 11. St. Clair, N.L.; Navia, M.A. J. Am. Chem. Soc. 1992, 114, 7314. Persichetti, R.A.; St. Clair, N.L.; Griffith, J.P.; Navia, M.A.; Margolin, A.L. J. Am. Chem. Soc. 1995, 117, 2732. Lalonde, J.J., Govardhan, C.P., Khalaf, N.K., Martinez, O.G., Visuri, K.J., Margolin, A.M., J. Am. Chem. Soc., 1995, 117, 6845.
28. 12. Subtilisin-CLEC (PeptiCLEC™-BL) is a commercial product of Altus Biologics.
29. 18 column (4.6 × 50 mm, 5 m, 300A), Mobile phase: gradient, ratio (v/v) of water (with 0.1 % trifluoroacetic acid) and acetonitrile (with 0.1 % trifluoroacetic acid) was 90:10 at 0 minute, 20:80 at 10 minute, 20:80 at 12 minute and 90:10 at 15 minute; Flow rate: 1 mL/ minute; UV detection at 254 nm; Retention times: amine, 2b: 3.88 min., NCbz Phe OBzl: 9.43 min., alkylamide, S,S-3a: 9.18 min., S,R-3a: 9.21 min., benzylalcohol: 2.72 min.
30. 1H NMR
31. 15. After each reaction cycle, the catalysts were filtered off and washed with 3-methyl-3-pentanol. The washed catalysts were directly used in the next cycle.