A highly efficient route to dehydroalanine containing peptides

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2831-2834

  Burrage, Sarah A ^a   Raynham, Tony ^b   Bradley, Mark ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROALANINE; PEPTIDE DERIVATIVE;

ANTIBIOTIC THERAPY; ARTICLE; DEHYDRATION; DRUG OXIDATION; DRUG SYNTHESIS; PEPTIDE SYNTHESIS;

EID: 0032580407     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00258-5     Document Type: Article

References (17)

1. 1. Schmidt, U., Lieberknecht, A., Wild, J., Synthesis, 1988, 159-172. Shin, C., Nakamura, Y., Okumura, K., Chem. Lett., 1993, 1405-1408. Fukase, K., Kitazawa, M., Sano, A., Shimbo, K., Horimoto, S., Fujita, H., Kubo, A., Wakamiya, T., Shiba, T., Bull. Chem. Soc. Jpn., 1992, 65, 2227-2240.
2. 1. Schmidt, U., Lieberknecht, A., Wild, J., Synthesis, 1988, 159-172. Shin, C., Nakamura, Y., Okumura, K., Chem. Lett., 1993, 1405-1408. Fukase, K., Kitazawa, M., Sano, A., Shimbo, K., Horimoto, S., Fujita, H., Kubo, A., Wakamiya, T., Shiba, T., Bull. Chem. Soc. Jpn., 1992, 65, 2227-2240.
3. 1. Schmidt, U., Lieberknecht, A., Wild, J., Synthesis, 1988, 159-172. Shin, C., Nakamura, Y., Okumura, K., Chem. Lett., 1993, 1405-1408. Fukase, K., Kitazawa, M., Sano, A., Shimbo, K., Horimoto, S., Fujita, H., Kubo, A., Wakamiya, T., Shiba, T., Bull. Chem. Soc. Jpn., 1992, 65, 2227-2240.
4. 2. Sahl, H.G., Jack, R.W., Bierbaum, G., Eur. J. Biochem., 1995, 230, 827-853. Jung. G., Angew. Chem. Int. Ed. Engl., 1991, 30, 1051-1065.
5. 2. Sahl, H.G., Jack, R.W., Bierbaum, G., Eur. J. Biochem., 1995, 230, 827-853. Jung. G., Angew. Chem. Int. Ed. Engl., 1991, 30, 1051-1065.
6. 3. Palmer, D.E., Pattaroni, C., Nunami, K., Chadha, R.K., Goodman, M., Wakamiya, T., Fukase, K., Horimoto, S., Kitazawa, M., Fujita, H., Kubo, A., Shiba, T., J. Am. Chem. Soc., 1992, 114, 5634-5642. Pietrzynski, G., Rzeszotarska, B., Polish J. Chem., 1995, 69, 1595-1614.
7. 3. Palmer, D.E., Pattaroni, C., Nunami, K., Chadha, R.K., Goodman, M., Wakamiya, T., Fukase, K., Horimoto, S., Kitazawa, M., Fujita, H., Kubo, A., Shiba, T., J. Am. Chem. Soc., 1992, 114, 5634-5642. Pietrzynski, G., Rzeszotarska, B., Polish J. Chem., 1995, 69, 1595-1614.
8. 4. Giannis, A., Kolter. T., Angew. Chem. Int. Ed. Engl., 1993, 32, 1244-1267.
9. 5. See for example, Miller, M., J. Org. Chem., 1980, 45, 3131-3132. Cherney, R.J., Wang, L., J.Org.Chem., 1996, 61, 2544-2546.
10. 5. See for example, Miller, M., J. Org. Chem., 1980, 45, 3131-3132. Cherney, R.J., Wang, L., J.Org.Chem., 1996, 61, 2544-2546.
11. 6. Scaloni, A., Barra, D., Bossa, F., Anal. Biochem. 1994, 218, 226-228.
12. 7. Hashimoto, K., Sakai, M., Okuno, T., Shirahama, H., Chem. Commun, 1996, 1139-1140.
13. 8. Yamada, M., Miyajima, T., Horikawa, H., Tetrahedron lett. 1998, 39, 289-292.
14. 2 Calc. 925.4626, found 925.4709.
15. 10. Elimination protocols: (a). The peptide 2a (2.9g; 6.1mmol) was dissolved in methanol (15ml), DBU (2.22g; 2.18ml; 2 equivalents) was added and the mixture stirred for one hour before being concentrated in vacua over a cold water bath. The residue was dissolved in ethyl acetate (5ml), filtered through a silica plug and concentrated in vacua to give the desired product as a colourless glass. Yield: 2.41g; 98%.
16. (b). The peptide 2a or b (100mg) was dissolved in dioxane (10ml) and refluxed for 15 hours before being concentrated in vacua. The residue was dissolved in ethyl acetate (2ml), filtered through a silica plug and concentrated in vacua to give the desired product as a colourless glass. Yields 3a: 75mg; 88%; 3b: 69mg; 84%
17. 12 Calc. 783.4504, found 783.4559.