메뉴 건너뛰기




Volumn 13, Issue 1-2, 2007, Pages 355-366

Alcohols as replacements of the central amide in β-turns, synthesis of Pro-Aib hydroxyethylene isostere and analysis in model β-turn peptides

Author keywords

Beta turn mimic; Hydroxy ethylene isostere; Pro aib mimic

Indexed keywords

2 METHYL 1 PROPENYLMAGNESIUM BROMIDE; ALCOHOL; ALKENE; AMIDE; AMINE; BROMINE DERIVATIVE; CARBAMIC ACID; ETHYLENE DERIVATIVE; HYDROGEN; HYDROXYL GROUP; KETONE; OXAZOLIDINONE DERIVATIVE; PEPTIDE; UNCLASSIFIED DRUG;

EID: 34249982333     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-007-9093-0     Document Type: Article
Times cited : (11)

References (21)
  • 1
    • 0001625628 scopus 로고    scopus 로고
    • A His-Pro-Aib peptide that exhibits an Asx-Pro-turn-like structure
    • Blank, J. T., Guerin, D. J., Miller, S. J.: 2000, A His-Pro-Aib peptide that exhibits an Asx-Pro-turn-like structure. Org. Lett. 2, 1247-1249
    • (2000) Org. Lett. , vol.2 , pp. 1247-1249
    • Blank, J.T.1    Guerin, D.J.2    Miller, S.J.3
  • 2
    • 0015552433 scopus 로고
    • Stable conformations of dipeptides
    • Burgess, A. W., Scheraga, H. A.: 1973, Stable conformations of dipeptides. Biopolymers 12, 2177-2183
    • (1973) Biopolymers , vol.12 , pp. 2177-2183
    • Burgess, A.W.1    Scheraga, H.A.2
  • 3
    • 0033541110 scopus 로고    scopus 로고
    • β-turn and β-hairpin mimicry with tetrasubstituted alkenes
    • Gardner, R. B., Liang, G.-B., Gellman, S. H.: 1999, β-turn and β-hairpin mimicry with tetrasubstituted alkenes. J. Am. Chem. Soc. 121, 1806-1816
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1806-1816
    • Gardner, R.B.1    Liang, G.-B.2    Gellman, S.H.3
  • 4
    • 0000802654 scopus 로고
    • Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: Variable-temperature NMR and IR studies an a homologous diamide series
    • Gellman, S. H., Dado, G. P., Liang, G., Adams, B. R.: 1991, Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: variable-temperature NMR and IR studies an a homologous diamide series. J. Am. Chem. Soc. 113, 1164-1173
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1164-1173
    • Gellman, S.H.1    Dado, G.P.2    Liang, G.3    Adams, B.R.4
  • 5
    • 0346422358 scopus 로고    scopus 로고
    • One-pot synthesis of homoallylic ketones from the addition of vinyl Grignard reagent to carboxylic esters
    • Hansford, K. A., Dettwiler, J. E. Lubell, W. D.: 2003, One-pot synthesis of homoallylic ketones from the addition of vinyl Grignard reagent to carboxylic esters. Org. Lett. 5, 4887-4890
    • (2003) Org. Lett. , vol.5 , pp. 4887-4890
    • Hansford, K.A.1    Dettwiler, J.E.2    Lubell, W.D.3
  • 6
    • 0000161519 scopus 로고
    • (1S,2R,8aS)-1,2-Dihydroxyindolizidine formation by Rhizoctonia leguminicola, the fungus that produces slaframine and swainsonine
    • Harris, T. M., Harris, C. M., Hill, J. E., Ungemach F. S., Broquist, H. P. Wickwire B. M.: 1987, (1S,2R,8aS)-1,2-Dihydroxyindolizidine formation by Rhizoctonia leguminicola, the fungus that produces slaframine and swainsonine. J. Org. Chem. 52, 3094-3098
    • (1987) J. Org. Chem. , vol.52 , pp. 3094-3098
    • Harris, T.M.1    Harris, C.M.2    Hill, J.E.3    Ungemach, F.S.4    Broquist, H.P.5    Wickwire, B.M.6
  • 7
    • 0000983397 scopus 로고    scopus 로고
    • Enantio-and regioselective synthesis of a (Z)-alkene cis-proline mimic
    • Hart, S. A., Sabat, M. Etzkorn, F. A.: 1998, Enantio-and regioselective synthesis of a (Z)-alkene cis-proline mimic. J. Org. Chem. 63, 7580-7581
    • (1998) J. Org. Chem. , vol.63 , pp. 7580-7581
    • Hart, S.A.1    Sabat, M.2    Etzkorn, F.A.3
  • 9
    • 0035973710 scopus 로고    scopus 로고
    • Characterization of an NH-πinteraction in Co(III, ternary complexes with aromatic amino acids
    • Kumita, H., Kato, T., Jitsukawa, K., Einaga, H. Masuda, H.: 2001, Characterization of an NH-πinteraction in Co(III, ternary complexes with aromatic amino acids. Inorg. Chem. 40, 3936-3942
    • (2001) Inorg. Chem. , vol.40 , pp. 3936-3942
    • Kumita, H.1    Kato, T.2    Jitsukawa, K.3    Einaga, H.4    Masuda, H.5
  • 10
    • 0034628448 scopus 로고    scopus 로고
    • Protease inhibitors: Current status and future prospects
    • Leung, D., Abbenante, G. Fairlie, D. P.: 2000, Protease inhibitors: current status and future prospects. J. Med. Chem. 43, 305-341
    • (2000) J. Med. Chem. , vol.43 , pp. 305-341
    • Leung, D.1    Abbenante, G.2    Fairlie, D.P.3
  • 11
    • 0345148379 scopus 로고    scopus 로고
    • Stereoselective synthesis of trifluoromethylated compounds: Nucleophilic addition of formaldehyde N,N-dialkylhydrazones to trifluoromethyl ketones
    • Pareja, C., Martin-Zamora, E., Fernàndez, R., Lassaletta, J. M.: 1999, Stereoselective synthesis of trifluoromethylated compounds: nucleophilic addition of formaldehyde N,N-dialkylhydrazones to trifluoromethyl ketones. J. Org. Chem. 64, 8846-8854
    • (1999) J. Org. Chem. , vol.64 , pp. 8846-8854
    • Pareja, C.1    Martin-Zamora, E.2    Fernàndez, R.3    Lassaletta, J.M.4
  • 12
    • 0029794253 scopus 로고    scopus 로고
    • Peptide models. 18. Hydroxymethyl side-chain induced backbone conformational shifts of L-serine amide. All ab initio conformers of for-l-Ser-NH2
    • Perczel, A., Farkas, O., Csizmadia, I. G.: 1996, Peptide models. 18. Hydroxymethyl side-chain induced backbone conformational shifts of L-serine amide. All ab initio conformers of for-l-Ser-NH2. J. Am. Chem. Soc. 118, 7809-7817
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7809-7817
    • Perczel, A.1    Farkas, O.2    Csizmadia, I.G.3
  • 13
    • 0037648871 scopus 로고    scopus 로고
    • Design of β-turn based therapeutic agents
    • Suat, K. K., Seetharama, D. S. J.: 2003, Design of β-turn based therapeutic agents. Curr. Pharm. Des. 9, 1209-1224
    • (2003) Curr. Pharm. Des. , vol.9 , pp. 1209-1224
    • Suat, K.K.1    Seetharama, D.S.J.2
  • 14
    • 0002973705 scopus 로고    scopus 로고
    • Comparison of an HXH three-center hydrogen bond with alternative two-center hydrogen bonds in a model system
    • 1
    • Yang, J., Christianson, L. A., Gellman, S. H.: 1999, Comparison of an HXH three-center hydrogen bond with alternative two-center hydrogen bonds in a model system. Org. Lett. 1(1), 11-13
    • (1999) Org. Lett. , vol.1 , pp. 11-13
    • Yang, J.1    Christianson, L.A.2    Gellman, S.H.3
  • 15
    • 0035800352 scopus 로고    scopus 로고
    • Incorporation of peptide isosteres into enantioselective peptide-based catalysts as mechanistic probes
    • Vasbinder, M. M., Jarvo, E. R., Miller, S. J.: 2001, Incorporation of peptide isosteres into enantioselective peptide-based catalysts as mechanistic probes. Angew. Chem. Int. Ed. 40, 2824-2827
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2824-2827
    • Vasbinder, M.M.1    Jarvo, E.R.2    Miller, S.J.3
  • 16
    • 0014347799 scopus 로고
    • Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide units
    • Venkatachalam, C. M.: 1968, Stereochemical criteria for polypeptides and proteins. V. Conformation of a system of three linked peptide units. Biopolymers 6, 1425-1436
    • (1968) Biopolymers , vol.6 , pp. 1425-1436
    • Venkatachalam, C.M.1
  • 17
    • 0020491942 scopus 로고
    • Conformational analysis of small disulfide loops. Spectroscopic and theoretical studies on a synthetic cyclic tetrapeptide containing cystine
    • Venkatachalapathi, Y. V., Venkataram Prasad, B. V., Balaram, P.: 1982, Conformational analysis of small disulfide loops. Spectroscopic and theoretical studies on a synthetic cyclic tetrapeptide containing cystine. Biochemistry 21, 5502-5509
    • (1982) Biochemistry , vol.21 , pp. 5502-5509
    • Venkatachalapathi, Y.V.1    Venkataram Prasad, B.V.2    Balaram, P.3
  • 19
    • 28144436378 scopus 로고    scopus 로고
    • Preorganization of the hydroxyethylene dipeptide isostere: The preferred conformation in solution resembles the conformation bound to BACE
    • Vidal, P., Timm, D., Broughton, H., Chen, S. H., Martin, J. A., Rivera-Sagredo, A., McCarthy, J. R., Shapiro, M. J., Espinosa, J. F.: 2005, Preorganization of the hydroxyethylene dipeptide isostere: the preferred conformation in solution resembles the conformation bound to BACE. J. Med. Chem. 48, 7623-7627
    • (2005) J. Med. Chem. , vol.48 , pp. 7623-7627
    • Vidal, P.1    Timm, D.2    Broughton, H.3    Chen, S.H.4    Martin, J.A.5    Rivera-Sagredo, A.6    McCarthy, J.R.7    Shapiro, M.J.8    Espinosa, J.F.9
  • 20
    • 0030781309 scopus 로고    scopus 로고
    • A rationale for the absolute conservation of Asn70 and Pro71 in mitochondrial cytochromes C suggested by protein engineering
    • Wallace, C. J. A. and Clark-Lewis, I.: 1997, A rationale for the absolute conservation of Asn70 and Pro71 in mitochondrial cytochromes C suggested by protein engineering. Biochemistry 36, 14733-14740
    • (1997) Biochemistry , vol.36 , pp. 14733-14740
    • Wallace, C.J.A.1    Clark-Lewis, I.2
  • 21
    • 0000428997 scopus 로고    scopus 로고
    • Methyl-and (trifluoromethyl)alkene peptide isosteres: Synthesis and evaluation of their potential as β-turn promoters and peptide mimetics
    • Wipf, P., Henninger, T. C., Geib, S. J.: 1998, Methyl-and (trifluoromethyl)alkene peptide isosteres: synthesis and evaluation of their potential as β-turn promoters and peptide mimetics. J. Org. Chem. 63, 6088-6089
    • (1998) J. Org. Chem. , vol.63 , pp. 6088-6089
    • Wipf, P.1    Henninger, T.C.2    Geib, S.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.