메뉴 건너뛰기




Volumn 12, Issue 2, 2006, Pages 154-160

New synthesis of cis 5-tert-butyl-L-proline via cuprate. Evaluation as a cis proline mimetic in a biological active octapeptide

Author keywords

Acyliminium; Cuprate; Peptide conformation; Peptide mimic; Proline analogue; Tert butyl proline

Indexed keywords

5 TERT BUTYLPROLINE; OCTAPEPTIDE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 32544442612     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.690     Document Type: Article
Times cited : (7)

References (23)
  • 1
    • 0022508899 scopus 로고
    • Study of an octadecaneuropeptide derived from diazepam binding inhibitor (DBI): Biological activity and presence in rat brain
    • Ferrero P, Santi MR, Conti-Tronconi B, Costa E, Guidotti A. Study of an octadecaneuropeptide derived from diazepam binding inhibitor (DBI): biological activity and presence in rat brain. Proc. Natl. Acad. Sci. U.S.A. 1986; 83: 827-831.
    • (1986) Proc. Natl. Acad. Sci. U.S.A. , vol.83 , pp. 827-831
    • Ferrero, P.1    Santi, M.R.2    Conti-Tronconi, B.3    Costa, E.4    Guidotti, A.5
  • 2
    • 0025719315 scopus 로고
    • Role of DBI in brain and its posttranslational processing products in normal and abnormal behavior
    • Guidotti A. Role of DBI in brain and its posttranslational processing products in normal and abnormal behavior. Neuropharmacology 1991; 30: 1425-1433.
    • (1991) Neuropharmacology , vol.30 , pp. 1425-1433
    • Guidotti, A.1
  • 3
    • 0035794025 scopus 로고    scopus 로고
    • The octadecaneuropeptide [diazepam-binding inhibitor (33-50)] exerts potent anorexigenic effects in rodents
    • Garcia de Mateos-Verchere J, Leprince J, Tonon MC, Vaudry H, Costentin J. The octadecaneuropeptide [diazepam-binding inhibitor (33-50)] exerts potent anorexigenic effects in rodents. Eur. J. Pharmacol. 2001; 414: 225-231.
    • (2001) Eur. J. Pharmacol. , vol.414 , pp. 225-231
    • Garcia de Mateos-Verchere, J.1    Leprince, J.2    Tonon, M.C.3    Vaudry, H.4    Costentin, J.5
  • 5
    • 0032487846 scopus 로고    scopus 로고
    • Structure-activity relationships of a series of analogues of the octadecaneuropeptide ODN on calcium mobilization in rat astrocytes
    • Leprince J, Gandolfo P, Thoumas JL, Patte C, Fauchère JL, Vaudry H, Tonon MC. Structure-activity relationships of a series of analogues of the octadecaneuropeptide ODN on calcium mobilization in rat astrocytes. J. Med. Chem. 1998; 41: 4433-4438.
    • (1998) J. Med. Chem. , vol.41 , pp. 4433-4438
    • Leprince, J.1    Gandolfo, P.2    Thoumas, J.L.3    Patte, C.4    Fauchère, J.L.5    Vaudry, H.6    Tonon, M.C.7
  • 7
    • 0030461902 scopus 로고    scopus 로고
    • Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-tert-butylproline N′-methylamides
    • Beausoleil E, Lubell WD. Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-tert-butylproline N′-methylamides. J. Am. Chem. Soc. 1996; 118: 12 902-12 908.
    • (1996) J. Am. Chem. Soc. , vol.118
    • Beausoleil, E.1    Lubell, W.D.2
  • 10
    • 0033367261 scopus 로고    scopus 로고
    • c-4-amino-t-3-hydroxy-r-1-cyclohexanecarboxylic acid and cis-4-amino-3-oxo-l-cyclohexane-carboxylic acid - mimetics of dipeptides with a twisted cis-amide bond
    • Krajewski K, Ciunik Z, Siemion IZ. c-4-amino-t-3-hydroxy-r-1-cyclohexanecarboxylic acid and cis-4-amino-3-oxo-l-cyclohexane-carboxylic acid - mimetics of dipeptides with a twisted cis-amide bond. Tetrahedron: Asymmetry 1999; 10: 4591-4598.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 4591-4598
    • Krajewski, K.1    Ciunik, Z.2    Siemion, I.Z.3
  • 11
    • 0000983397 scopus 로고    scopus 로고
    • Enantio- and regioselective synthesis of a (Z)-alkene cis-proline mimic
    • Hart SA, Sabat M, Etzkorn FA. Enantio- and regioselective synthesis of a (Z)-alkene cis-proline mimic. J. Org. Chem. 1998; 63: 7580-7581.
    • (1998) J. Org. Chem. , vol.63 , pp. 7580-7581
    • Hart, S.A.1    Sabat, M.2    Etzkorn, F.A.3
  • 13
    • 0025103048 scopus 로고
    • A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis
    • King DS, Fields CG, Fields GB. A cleavage method which minimizes side reactions following Fmoc solid phase peptide synthesis. Int. J. Peptide Protein Res. 1990; 36: 255-266.
    • (1990) Int. J. Peptide Protein Res. , vol.36 , pp. 255-266
    • King, D.S.1    Fields, C.G.2    Fields, G.B.3
  • 15
    • 0029117655 scopus 로고
    • Stereoselective addition of grignard-derived organocopper reagents to N-acyliminium ions: Synthesis of enantiopure 5- and 4,5-substituted prolinates
    • Collado I, Ezquerra J, Pedregal C. Stereoselective addition of grignard-derived organocopper reagents to N-acyliminium ions: synthesis of enantiopure 5- and 4,5-substituted prolinates. J. Org. Chem. 1995; 60: 5011-5015.
    • (1995) J. Org. Chem. , vol.60 , pp. 5011-5015
    • Collado, I.1    Ezquerra, J.2    Pedregal, C.3
  • 16
    • 0030040826 scopus 로고    scopus 로고
    • New routes to conformationally restricted peptide building blocks: A convenient preparation of bicyclic piperazinone derivatives
    • Fobian YM, d'Avignon DA, Moeller KD. New routes to conformationally restricted peptide building blocks: a convenient preparation of bicyclic piperazinone derivatives. Bioorg. Med. Chem. Lett. 1996; 6: 315-318.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 315-318
    • Fobian, Y.M.1    d'Avignon, D.A.2    Moeller, K.D.3
  • 17
    • 0032572841 scopus 로고    scopus 로고
    • Synthesis of indolizidines (-)-195B, (-)223AB and (-)-239AB: (2S,5R)-1-[(benzyloxy)carbonyl]-2- methoxycarbonyl-5-(4-pentenyl)pyrrolidine as a versatile chiral building block
    • Célimène C, Dhimane H, Lhommet G. Synthesis of indolizidines (-)-195B, (-)223AB and (-)-239AB: (2S,5R)-1-[(benzyloxy)carbonyl]-2- methoxycarbonyl-5-(4-pentenyl)pyrrolidine as a versatile chiral building block. Tetrahedron 1998; 54: 10 457-10 468.
    • (1998) Tetrahedron , vol.54
    • Célimène, C.1    Dhimane, H.2    Lhommet, G.3
  • 18
    • 0035939187 scopus 로고    scopus 로고
    • Improved synthesis of (2S,5S)-5-tert-butylproline
    • Halab L, Belec L, Lubell WD. Improved synthesis of (2S,5S)-5-tert-butylproline. Tetrahedron 2001; 57: 6439-6446.
    • (2001) Tetrahedron , vol.57 , pp. 6439-6446
    • Halab, L.1    Belec, L.2    Lubell, W.D.3
  • 21
    • 0034612979 scopus 로고    scopus 로고
    • 1-Ethyl 2-halopyridinium salts, highly efficient coupling reagents for hindered peptide synthesis both in solution and the solid-phase
    • Li P, Xu JC. 1-Ethyl 2-halopyridinium salts, highly efficient coupling reagents for hindered peptide synthesis both in solution and the solid-phase. Tetrahedron 2000; 56: 8119-8131.
    • (2000) Tetrahedron , vol.56 , pp. 8119-8131
    • Li, P.1    Xu, J.C.2
  • 23
    • 0033617257 scopus 로고    scopus 로고
    • Use of steric interactions to control peptide turn geometry. Synthesis of type VI β-turn mimics with 5-tert-butylproline
    • Halab L, Lubell WD. Use of steric interactions to control peptide turn geometry. Synthesis of type VI β-turn mimics with 5-tert-butylproline. J. Org. Chem. 1999; 64: 3312-3321.
    • (1999) J. Org. Chem. , vol.64 , pp. 3312-3321
    • Halab, L.1    Lubell, W.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.