Direct synthesis of N-protected β-amino dimethylhydroxamates: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate ψ[CH2CH2NH]

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4239-4242

  Limal, David ^a   Quesnel, Anne ^a   Briand, Jean Paul ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

Author keywords

Peptide analogues mimetics; Rearrangements; Solid phase synthesis

Indexed keywords

BETA AMINO DIMETHYLHYDROXAMATE; HYDROXAMIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; AMINO TERMINAL SEQUENCE; ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN ASSEMBLY; PROTEIN MODIFICATION; SOLID PHASE EXTRACTION;

EID: 0032508074     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00675-3     Document Type: Article

References (20)

1. [1] Sone O, Nemoto T, Ishiwata H, Ojika M, Yamada K. Tetrahedron Lett. 1993; 34: 8449-8452.
2. [2] Seebach D, Overhand M, Kühnle F, Martinoni B, Oberer L, Hommel U, Widmer, H. Helv.Chim.Acta 1996; 79: 913-941.
3. [3] Seebach D, Ciceri P, Overhand M, Jaun B, Rigo D, Oberer L, Hommel U, Amstutz R, Widmer H. Helv. Chim. Acta 1996; 79: 2043-2066.
4. [4] Apella DH, Christianson LA, Klein IL, Powell DR, Huang JJ, Barchi J, Gellman SH Nature 1997; 387, 381-384.
5. [5] Seebach, D. & Matthews, J.L. Chem.Commun. 1997: 2015-2022.
6. [6] Hintermann T, Seebach D. Chimia 1997; 50: 244-247.
7. [7] Spatola AF, Peptide Backbone Modifications. In: Weinstein B, editor. Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins. New York, Marcel Dekker, 1983; 7: 267-357.
8. [8] Marraud M, Aubry A. Biopolymers 1996: 40: 45-83.
9. [9] Rodriguez M, Aumelas A, Martinez J. Tetrahedron Lett. 1990; 31: 5153-5156.
10. [10] Caution: The generation and the handling of diazomethane requires special precautions [20].
11. [11] Podlech J, Seebach D. Liebigs Ann. 1995: 1217-1228.
12. [12] Podlech J, Seebach D. Angew. Chem. Int. Ed. Eng. 1995; 34: 471-472.
13. [13] Guibourdenche C, Seebach D, Natt F. Helv. Chem. Acta 1997; 80: 1-13.
14. [14] Brown F, Benkirane N, Limal D, Halimi H, Newman JFE, Van Regenmortel MHV, Briand JP, Muller S. submitted.
15. [15] Neimark J, Briand JP. Peptide Res. 1993; 6: 219-228.
16. [16] Fehrentz J, Castro B. Synthesis 1983: 676-678.
17. [17] Sasaki Y, Coy DH. Peptides 1987; 8: 119-121.
18. [18] Leggio A, Liguori A, Procopio C, Siciliano C, Sindona G. J. Chem.Soc.Perkin Trans I 1997: 1969-1971.
19. [19] King D, Fields C, Fields G. Int. J. Pept. Prot. Res. 1990; 36: 255-266.
20. [20] Moss S. Chem. Ind. 1994: 122.