메뉴 건너뛰기




Volumn 14, Issue 9, 2008, Pages 1051-1061

New 21 - and 24-atom Aib-containing cyclopeptides

Author keywords

Aib peptides; Crystal structure; Cyclopeptides; Peptide synthesis

Indexed keywords

CYCLOGLYCYLVALYLLEUCYLPHENYLALANINE ALPHA AMINOISOBUTYRIC ACID; CYCLOLEUCYLPHENYLGLYCYLPHENYLALANINE ALPHA AMINOISOBUTYRIC ACID; CYCLOPEPTIDE; HEPTAPEPTIDE; OCTAPEPTIDE; REAGENT; UNCLASSIFIED DRUG;

EID: 53349174437     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1041     Document Type: Article
Times cited : (14)

References (43)
  • 2
    • 0036254144 scopus 로고    scopus 로고
    • Current synthetic approaches to peptide and peptidomimetic cyclization
    • Li P, Roller PP, Xu J. Current synthetic approaches to peptide and peptidomimetic cyclization. Curr. Org. Chem. 2002; 6: 411-440.
    • (2002) Curr. Org. Chem , vol.6 , pp. 411-440
    • Li, P.1    Roller, P.P.2    Xu, J.3
  • 3
    • 0041475925 scopus 로고    scopus 로고
    • The cyclization of peptides and depsipeptides
    • Davies JS. The cyclization of peptides and depsipeptides. J. Pept. Sci. 2003; 9: 471-501.
    • (2003) J. Pept. Sci , vol.9 , pp. 471-501
    • Davies, J.S.1
  • 4
    • 11844269831 scopus 로고    scopus 로고
    • A straightforward approach towards cyclic peptides via ring-closing metathesis - scope and limitation
    • Kazmeier U, Hebach C, Watzke A, Maier S, Mues H, Huch V. A straightforward approach towards cyclic peptides via ring-closing metathesis - scope and limitation. Org. Biomol. Chem. 2005; 3: 136-145.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 136-145
    • Kazmeier, U.1    Hebach, C.2    Watzke, A.3    Maier, S.4    Mues, H.5    Huch, V.6
  • 5
    • 23944526356 scopus 로고    scopus 로고
    • A safety catch linker for Fmoc-based assembly of constrained cyclic peptides
    • Ravn J, Bourne GT, Smythe ML. A safety catch linker for Fmoc-based assembly of constrained cyclic peptides. J. Pept. Sci. 2005; 11: 572-578.
    • (2005) J. Pept. Sci , vol.11 , pp. 572-578
    • Ravn, J.1    Bourne, G.T.2    Smythe, M.L.3
  • 6
    • 33750884444 scopus 로고    scopus 로고
    • Synthesis of cyclic peptides constrained with biarylamine linkers using Buchwald-Hartwig C-N coupling
    • Balraju V, Iqbal J. Synthesis of cyclic peptides constrained with biarylamine linkers using Buchwald-Hartwig C-N coupling. J. Org. Chem. 2006; 71: 8954-8956.
    • (2006) J. Org. Chem , vol.71 , pp. 8954-8956
    • Balraju, V.1    Iqbal, J.2
  • 7
    • 35348923536 scopus 로고    scopus 로고
    • Synthesis of cyclic peptides and peptide libraries on an new disulfide linker
    • Tegge W, Bautsch W, Frank R. Synthesis of cyclic peptides and peptide libraries on an new disulfide linker, J. Pept. Sci. 2007; 18: 693-699.
    • (2007) J. Pept. Sci , vol.18 , pp. 693-699
    • Tegge, W.1    Bautsch, W.2    Frank, R.3
  • 8
    • 35248839338 scopus 로고    scopus 로고
    • Supramolecular approach for synthesis and functionalization of cyclic macromolecules
    • Oike H. Supramolecular approach for synthesis and functionalization of cyclic macromolecules. React. Fuct. Polym. 2007; 67: 1157-1167.
    • (2007) React. Fuct. Polym , vol.67 , pp. 1157-1167
    • Oike, H.1
  • 11
    • 14044262886 scopus 로고    scopus 로고
    • Cyclization of peptides
    • Goodman M, Felix A, Moroder L, Toniolo C eds, Thieme Publisher: Stuttgart
    • Gilon C, Mang C, Lohof E, Friedler A, Kessler H. Cyclization of peptides. In Houben-Weyl Methods of Organic Chemistry, Vol. E22b, Goodman M, Felix A, Moroder L, Toniolo C (eds). Thieme Publisher: Stuttgart, 2003; 461-542.
    • (2003) Houben-Weyl Methods of Organic Chemistry , vol.E22b , pp. 461-542
    • Gilon, C.1    Mang, C.2    Lohof, E.3    Friedler, A.4    Kessler, H.5
  • 12
    • 11244282839 scopus 로고    scopus 로고
    • Solution-phase synthesis of Aib-containing cyclic hexapeptides
    • Jeremic T, Linden A, Heimgartner H. Solution-phase synthesis of Aib-containing cyclic hexapeptides. Chem. Biodivers. 2004; 1: 1730-1761.
    • (2004) Chem. Biodivers , vol.1 , pp. 1730-1761
    • Jeremic, T.1    Linden, A.2    Heimgartner, H.3
  • 13
    • 11244318259 scopus 로고    scopus 로고
    • Synthesis of cyclohexapeptides containing Pro and Aib residues
    • Jeremic T, Linden A, Heimgartner H. Synthesis of cyclohexapeptides containing Pro and Aib residues. Helv. Chim. Acta 2004; 87: 3056-3079.
    • (2004) Helv. Chim. Acta , vol.87 , pp. 3056-3079
    • Jeremic, T.1    Linden, A.2    Heimgartner, H.3
  • 14
    • 12944307840 scopus 로고    scopus 로고
    • Synthesis and conformational analysis of 18-membered Aib-containing cyclohexapeptides
    • Jeremic T, Linden A, Moehle K, Heimgartner H. Synthesis and conformational analysis of 18-membered Aib-containing cyclohexapeptides. Tetrahedron 2005; 61: 1871-1883.
    • (2005) Tetrahedron , vol.61 , pp. 1871-1883
    • Jeremic, T.1    Linden, A.2    Moehle, K.3    Heimgartner, H.4
  • 15
    • 0030470879 scopus 로고    scopus 로고
    • Cyclization of all-L-pentapeptides by means of 1-hydroxy-7-azabenzotriazole-derived uronium and phosphonium reagents
    • Ehrlich A, Heyne HU, Winter R, Beyermann M, Haber H, Carpino LA, Bienert M. Cyclization of all-L-pentapeptides by means of 1-hydroxy-7-azabenzotriazole-derived uronium and phosphonium reagents. J. Org. Chem. 1996; 61: 8831-8838.
    • (1996) J. Org. Chem , vol.61 , pp. 8831-8838
    • Ehrlich, A.1    Heyne, H.U.2    Winter, R.3    Beyermann, M.4    Haber, H.5    Carpino, L.A.6    Bienert, M.7
  • 16
    • 53349173499 scopus 로고
    • Konformationsuntersuchungen an vier cyclischen Heptapeptiden durch NMR-Spektroskopie.
    • Kessler H, Bernd M. Konformationsuntersuchungen an vier cyclischen Heptapeptiden durch NMR-Spektroskopie. Liebigs Ann. Chem. 1985; 1145-1167.
    • (1985) Liebigs Ann. Chem , pp. 1145-1167
    • Kessler, H.1    Bernd, M.2
  • 17
    • 0242660944 scopus 로고    scopus 로고
    • Solid-phase total synthesis of scytalidamide A
    • Gu W, Silverman RB. Solid-phase total synthesis of scytalidamide A. J. Org. Chem. 2003; 68: 8774-8779.
    • (2003) J. Org. Chem , vol.68 , pp. 8774-8779
    • Gu, W.1    Silverman, R.B.2
  • 19
    • 0034901615 scopus 로고    scopus 로고
    • New optically active 2H-azirin-3-amines as synthons for enantiomerically pure 2,2-disubstituted glycines
    • Brun KA, Linden A, Heimgartner H. New optically active 2H-azirin-3-amines as synthons for enantiomerically pure 2,2-disubstituted glycines. Helv. Chim. Acta 2001; 84: 1756-1777.
    • (2001) Helv. Chim. Acta , vol.84 , pp. 1756-1777
    • Brun, K.A.1    Linden, A.2    Heimgartner, H.3
  • 20
    • 0032701312 scopus 로고    scopus 로고
    • Lehmann J, Heimgartner H. Synthesis of endothiopeptides and their cyclization to 1,3-thiazol-5(4H)-imines. Helv. Chim. Acta 1999; 82: 1899-1915.
    • Lehmann J, Heimgartner H. Synthesis of endothiopeptides and their cyclization to 1,3-thiazol-5(4H)-imines. Helv. Chim. Acta 1999; 82: 1899-1915.
  • 22
    • 84977289324 scopus 로고
    • An empirical correction for absorption anisotropy
    • Blessing RH. An empirical correction for absorption anisotropy. Acta Crystallogr., Sect. A 1995; 51: 33-38.
    • (1995) Acta Crystallogr., Sect. A , vol.51 , pp. 33-38
    • Blessing, R.H.1
  • 25
    • 84942435207 scopus 로고
    • BYPASS: An effective method for the refinement of crystal structures containing disordered solvent regions
    • van der Sluis P, Spek AL. BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions. Acta Crystallogr. 1990; A46: 194-201.
    • (1990) Acta Crystallogr , vol.A46 , pp. 194-201
    • van der Sluis, P.1    Spek, A.L.2
  • 27
    • 0034474897 scopus 로고    scopus 로고
    • Reporting and evaluating absolute-structure and absolute-configuration determinations
    • Flack HD, Bernardinelli G. Reporting and evaluating absolute-structure and absolute-configuration determinations. J. Appl. Crystallogr. 2000; 33:1143-1148.
    • (2000) J. Appl. Crystallogr , vol.33 , pp. 1143-1148
    • Flack, H.D.1    Bernardinelli, G.2
  • 29
    • 19944425329 scopus 로고
    • Coherent X-ray scattering for hydrogen atom in hydrogen molecule
    • Stewart RF, Davidson ER, Simpson WT. Coherent X-ray scattering for hydrogen atom in hydrogen molecule. J. Chem Phys. 1965; 42: 3175-3187.
    • (1965) J. Chem Phys , vol.42 , pp. 3175-3187
    • Stewart, R.F.1    Davidson, E.R.2    Simpson, W.T.3
  • 30
    • 0000940732 scopus 로고
    • Dispersion corrections + crystal structure refinements
    • Ibers JA, Hamilton WC. Dispersion corrections + crystal structure refinements. Acta Crystallogr. 1964; 17: 781-782.
    • (1964) Acta Crystallogr , vol.17 , pp. 781-782
    • Ibers, J.A.1    Hamilton, W.C.2
  • 31
  • 32
  • 34
    • 0032567305 scopus 로고    scopus 로고
    • Use of onium salt-based coupling reagents in pepide synthesis
    • Albericio F, Bofill JM, El-Faham A, Kates SA. Use of onium salt-based coupling reagents in pepide synthesis. J. Org. Chem. 1998; 68: 9678-9683.
    • (1998) J. Org. Chem , vol.68 , pp. 9678-9683
    • Albericio, F.1    Bofill, J.M.2    El-Faham, A.3    Kates, S.A.4
  • 35
    • 0037064593 scopus 로고    scopus 로고
    • Total syntheses of lyngbyabellins A and B, potent cytotoxic lipopeptides from the marine cyanobacterium Lyngbya majuscula
    • Yokokawa F, Sameshima H, Katagiri D, Aoyama T, Shioiri T. Total syntheses of lyngbyabellins A and B, potent cytotoxic lipopeptides from the marine cyanobacterium Lyngbya majuscula. Tetrahedron 2002; 58: 9445-9458.
    • (2002) Tetrahedron , vol.58 , pp. 9445-9458
    • Yokokawa, F.1    Sameshima, H.2    Katagiri, D.3    Aoyama, T.4    Shioiri, T.5
  • 36
    • 0035686407 scopus 로고    scopus 로고
    • New reagents, reactions, and peptidomimetics for drug design
    • Goodman M, Zapf C, Rew Y. New reagents, reactions, and peptidomimetics for drug design. Biopolymers 2001; 66: 229-245.
    • (2001) Biopolymers , vol.66 , pp. 229-245
    • Goodman, M.1    Zapf, C.2    Rew, Y.3
  • 39
    • 33748502022 scopus 로고
    • Patterns in hydrogen bonding-functionality and graph set analysis in crystals
    • Bernstein J, Davis RE, Shimoni L, Chang N-L. Patterns in hydrogen bonding-functionality and graph set analysis in crystals. Angew. Chem., Int. Ed. Engl. 1995; 34: 1555-1573.
    • (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 1555-1573
    • Bernstein, J.1    Davis, R.E.2    Shimoni, L.3    Chang, N.-L.4
  • 40
    • 0021779081 scopus 로고    scopus 로고
    • Rose GD, Gierasch LM, Smith JA. Turns in peptides and proteins. Adv. Protein Chem. 1985; 37: 1-109.
    • Rose GD, Gierasch LM, Smith JA. Turns in peptides and proteins. Adv. Protein Chem. 1985; 37: 1-109.
  • 42
    • 0038808747 scopus 로고    scopus 로고
    • Conformation of cyclic peptides. Principle concepts and design of selectivity and superactivity in bioactive sequences by spatial screening
    • Kessler H, Gratias R, Hessler G, Gurrath M, Mueller G. Conformation of cyclic peptides. Principle concepts and design of selectivity and superactivity in bioactive sequences by spatial screening. Pure Appl. Chem. 1996; 68: 1201-1205.
    • (1996) Pure Appl. Chem , vol.68 , pp. 1201-1205
    • Kessler, H.1    Gratias, R.2    Hessler, G.3    Gurrath, M.4    Mueller, G.5
  • 43
    • 0017078891 scopus 로고
    • Conformation of the cyclic tetrapeptide dihydrochlamydocin. labu-L-Phe-D-Pro-LX, and experimental values for 3 → 1 intramolecular hydrogen bonds by X-ray diffraction
    • Flippen JL, Karle IL. Conformation of the cyclic tetrapeptide dihydrochlamydocin. labu-L-Phe-D-Pro-LX, and experimental values for 3 → 1 intramolecular hydrogen bonds by X-ray diffraction. Biopolymers 1976; 15: 1081-1092.
    • (1976) Biopolymers , vol.15 , pp. 1081-1092
    • Flippen, J.L.1    Karle, I.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.