Straightforward synthesis of N-hydroxy peptides

Synlett

Volumn , Issue 5, 2003, Pages 671-674

  Maire, Pascal ^a   Blandin, Véronique ^a   Lopez, Monique ^a   Vallée, Yannick ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Hydroxylamines; N O acylation; N hydroxy peptides; Oximes; Reduction

Indexed keywords

AMINO ACID; HYDROXYL GROUP; OXIME; PEPTIDE DERIVATIVE;

ARTICLE; CHROMATOGRAPHY; DIASTEREOISOMER; PROTEIN SYNTHESIS; REDUCTION; STEREOCHEMISTRY;

EID: 0037263901     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38347     Document Type: Article

References (35)

1. For reviews see: (a) Ottenheijm, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697. (b) Marraud, M.; Vanderesse, R. In Houben-Weyl, Methods of Organic Chemistry, 4th ed., Vol. E22c; Goodman, M., Ed.; Thieme: Stuttgart, 2002, .
2. For reviews see: (a) Ottenheijm, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697. (b) Marraud, M.; Vanderesse, R. In Houben-Weyl, Methods of Organic Chemistry, 4th ed., Vol. E22c; Goodman, M., Ed.; Thieme: Stuttgart, 2002, .
3. (a) Isolation and structure determination: Umezawa, K.; Nakazawa, K.; Ikeda, Y.; Naganawa, H.; Kondo, S. J. Org. Chem. 1999, 64, 3034.
4. (b) Biosynthesis of polyoxypeptin A: Umezawa, K.; Ikeda, Y.; Kawase, O.; Naganawa, H.; Kondo, S. J. Chem. Soc., Perkin Trans. 1 2001, 1550.
5. (a) Garrouste, P.; Pawlowski, M.; Tonnaire, T.; Sicsic, S.; Dumy, P.; de Rosny, E.; Reboud-Ravaux, M.; Fulcrand, P.; Martinez, J. Eur. J. Med. Chem. 1998, 33, 423.
6. (b) Marastoni, M.; Bazzaro, M.; Salvadori, S.; Bortolotti, F.; Tomatis, R. Bioorg. Med. Chem. 2001, 9, 939.
7. (a) Dupont, V.; Lecoq, A.; Mangeot, J.-P.; Aubry, A.; Boussard, G.; Marraud, M. J. Am. Chem. Soc. 1993, 115, 8898.
8. (b) Takeuchi, Y.; Marshall, G. R. J. Am. Chem. Soc. 1998, 120, 5363.
9. Selected examples: (a) Akiyama, M.; Katoh, A.; Mutsui, Y.; Watanabe, Y.; Umemoto, K. Chem. Lett. 1996, 915. (b) Hara, Y.; Akiyama, M. J. Am. Chem. Soc. 2001, 123, 7247.
10. Selected examples: (a) Akiyama, M.; Katoh, A.; Mutsui, Y.; Watanabe, Y.; Umemoto, K. Chem. Lett. 1996, 915. (b) Hara, Y.; Akiyama, M. J. Am. Chem. Soc. 2001, 123, 7247.
11. Kolosa, T.; Chimiak, A. Tetrahedron 1977, 33, 3285.
12. Formation of the N-benzyloxy amide link is very sensitive to steric hindrance and generally requires strong acylating systems such as HATU {N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N- methylmethanaminium hexafluorophosphate} see: (a) Akiyama, M.; Iesaki, K.; Katoh, A.; Shimizu, K. J. Chem. Soc., Perkin Trans. 1 1986, 851. (b) Bianco, A.; Zabel, C.; Walden, P.; Jung, G. J. Peptide Sci. 1998, 4, 471.
13. Formation of the N-benzyloxy amide link is very sensitive to steric hindrance and generally requires strong acylating systems such as HATU {N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N- methylmethanaminium hexafluorophosphate} see: (a) Akiyama, M.; Iesaki, K.; Katoh, A.; Shimizu, K. J. Chem. Soc., Perkin Trans. 1 1986, 851. (b) Bianco, A.; Zabel, C.; Walden, P.; Jung, G. J. Peptide Sci. 1998, 4, 471.
14. (a) Nucleophilic substitution on α-bromo acid: Kolasa, T.; Chimiak, A. Tetrahedron 1974, 30, 3591.
15. (b) Use of α-hydroxy acid via the triflate derivative: Feenstra, R. W.; Stokkingreef, E. H. M.; Nivard, R. J. F.: Ottenheijm, H. C. J. Tetrahedron 1988, 44, 5583.
16. (c) Under Mitsunobu conditions: Hanessian, S.; Yang, R.-Y. Synlett 1995, 633.
17. (d) Oxyamination of N-acylsultam enolate: Oppolzer, W.; Tamura, O.; Deerberg, J. Helv. Chim. Acta 1992, 75, 1965.
18. (e) Oxidation of α-amino acid derivatives: Grundke, G.; Keese, W.; Rimpler, M. Synthesis 1987, 1115.
19. (f) See also: Feenstra, R. W.; Stokkingreef, E. H. M.; Reichwein, A. M.; Lousberg, W. B. H.; Ottenheijm, H. C. J. Tetrahedron 1990, 46, 1745.
20. (g) See also: Detomaso, A.; Curci, R. Tetrahedron Lett. 2001, 42, 755.
21. Ottenheijm, H. C. J.; de Man, J. H. M. Synthesis 1975, 163.
22. The two oxime isomers are separated by liquid chromatography. No difference in diastereoselectivity was observed in their reduction so that they were used as a mixture.
23. Tijhuis, M. W.; Herscheid, J. D. M.; Ottenheijm, H. C. J. Synthesis 1980, 890.
24. Reduction of 2h with sodium cyanoborohydride was also inefficient.
25. -1): 3323 (m), 3254 (w), 2977 (m), 1738 (s), 1663 (s), 1541 (s).
26. 1H NMR) and 3.69 mmol of the second diastereomer.
27. See ref. 1 and references therein.
28. -1 ): 3316 (s br), 2964 (m), 1734 (s), 1701 (s), 1641 (s), 1533 (s), 1450 (s).
29. 3)-NH-O(CO)-].
30. Abbreviations: DCC, dicyclohexylcarbodiimide; HOBt, 1-hydroxybenzotriazole; EDCI, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide; BOP, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate; DMTMM, 4-(4, 6-dimethoxy[1,3,5]triazin-2-yl)-4-methyl-morpholinium chloride.
31. (a) Preparation of DMTMM: Kunishima, M.; Kawachi, C.; Morita, J.; Terao, K.; Iwasaki, F.; Tani, S. Tetrahedron 1999, 55, 13159.
32. (b) Use in the synthesis of hydroxamates: De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534.
33. (a) Reaction of N-alkyl hydroxylamine with mixed anhydrides of amino acids: Nakonieczna, L.; Chimiak, A. Synthesis 1987, 418.
34. (b) Acylation of optically active N-hydroxy Leucine methyl ester with simple acyl chlorides: Jin, Y.; Kim, D. H. Tetrahedron: Asymmetry 1997, 8, 3699.
35. 3 in a NMR tube with 3 equiv of pyridine indicates that with 0.7 equiv of TMSCl two exchanging products are first visible. After the addition of an excess TMSCl (up to 2.2 equiv), only one product remains. This is in agreement with previous findings (see ref. 20a).