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Volumn 9, Issue 18, 2003, Pages 4510-4522

Synthesis, structure and conformation of partially-modified retro- and retro-inverso ψ[NHCH(CF3)]Gly peptides

Author keywords

Conformation analysis; Fluorine; Michael addition; Peptidomimetics

Indexed keywords

CARBON; CARRIER CONCENTRATION; CRYSTAL STRUCTURE; ESTERS; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

EID: 10744227548     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304881     Document Type: Article
Times cited : (74)

References (123)
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    • e) M. D. Fletcher, M. M. Campbell, Chem. Rev. 1998, 98, 763-795. The idea of retropeptides originates from the fact that peptides and proteins, like other biopolymers, have a direction and therefore are inherently non-palindromic. The sense of direction conventionally proceeds from the amino terminus (which is written on the left, see Figure 1) to the carboxy terminus (written on the right).
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    • The retro- and retro-inverso peptide concepts are finding increasing applications in medicinal chemistry. For some examples: a) J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328-1335;
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    • note
    • 2OH.
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    • 3)]Gly peptides, as well as peptidyl hydroxamates having moderate inhibitory activity against MMP-9 (gelatinase B), have been already prepared through solid-phase synthesis: a) A. Volonterio, P. Bravo, N. Moussier, Zanda, M. Tetrahedron Lett. 2000, 41, 6517-6521;
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    • for a recent paper on a novel class of retropeptides incorporating a stereodefined 3,3,3-trifluoroalanine mimic: e) M. Sani, L. Bruché, G. Chiva, S. Fustero, J. Piera, A. Volonterio, M. Zanda, Angew. Chem. 2003, 115, 2106-2109; Angew. Chem. Int. Ed. 2003, 42, 2060-2063.
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    • 3 group and imide function. For other aza-Michael reactions with 4-substituted acceptors see: c) A. J. Burke, S. G. Davies, C. J. R. Hedgecock, Synlett 1996, 621-622;
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    • note
    • Diastereomerically pure 3 were smoothly isolated by flash chromatography on silica gel.
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    • note
    • 3)]Gly peptide"), while the stereochemistry of the other major diastereomers 3b-j was assigned on the basis of their spectral and chemical-physical similarities with 3a. The stereochemistry of 5a, major diastereomer derived from D-Ala-OMe la, was determined by chemical correlation with 3a after cleavage of the oxazolidinone auxiliary.
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    • note
    • Only proline derived pseudo-tripeptide 9d, obtained as a ca. 3:1 mixture of isomers at the peptide bond, and tetrapeptide 10 were isolated as foams.
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    • and references therein
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    • a) H. Kessler, Angew. Chem. 1982, 94, 509-520; Angew. Chem. Int. Ed. 1982, 512-523.
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    • a) H. Kessler, Angew. Chem. 1982, 94, 509-520; Angew. Chem. Int. Ed. 1982, 512-523.
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    • note
    • These compounds were obtained as described in ref. [7c].
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    • note
    • b chemical shifts of epimers 13 and 14 seems to be convergent at higher temperature, which is more than reasonable for two closely similar structures.
  • 105
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    • note
    • b. (equation presented)
  • 106
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    • note
    • Also, for 14 free MD calculations were performed and, after minimization without constraints, many different structures were obtained.
  • 107
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    • note
    • CCDC-204501-204503 (3a, 9a and 9c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)1223-336-033; or e-mail: deposit@ccdc.cam. ac.uk).
  • 109
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    • note
    • 3)]Gly peptides fall within this range, although they are quite large and shifted toward the upper limit value;
  • 110
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    • note
    • 3)]Gly peptides incorporate a framework B, mimic of the Gellman's retropeptide unit C (see ref. [19]). This is likely due to the fact that amide and imide carbonyls are much better hydrogen-bond acceptors than carbonyls belonging to ester functions. (equation presented)
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    • See ref. [17], pp. 537-538
    • See ref. [17], pp. 537-538.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.