메뉴 건너뛰기




Volumn 24, Issue 3, 2003, Pages 311-323

Solution phase synthesis of the 14-residue peptaibol antibiotic trichovirin I

Author keywords

Aminoisobutyric acid (Aib); Peptaibols; Peptide antibiotics; Peptide synthesis; Trichoderma viride; Trichovirin

Indexed keywords

2 AMINO 2 METHYLPROPIONIC ACID; PEPTAIBOL; TRICHOVIRIN I; UNCLASSIFIED DRUG;

EID: 17444439461     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-002-0401-x     Document Type: Article
Times cited : (21)

References (36)
  • 4
    • 0142210377 scopus 로고
    • Oxazolone activation in the synthesis of oligopeptides containing α-methylalanine
    • König WA, Voelter W (eds) Chemistry of peptides and proteins 4, 1987. Attempto, Tübingen
    • Brückner H (1989) Oxazolone activation in the synthesis of oligopeptides containing α-methylalanine. In: König WA, Voelter W (eds) Chemistry of peptides and proteins 4, 1987. Proceedings of the Sixth USSR-FRG Symposium on Chemistry of Peptides and Proteins. Attempto, Tübingen, pp 79-86
    • (1989) Proceedings of the Sixth USSR-FRG Symposium on Chemistry of Peptides and Proteins , pp. 79-86
    • Brückner, H.1
  • 5
    • 0038522195 scopus 로고
    • Methodologies for the synthesis of naturally occurring "peptaibol" antibiotics and conformationally designed analogs
    • Aubry A, Marraud M, Vitoux B (eds). Colloque INSERM/John Libbey Eurotext Ltd
    • Brückner H, Currle M (1989) Methodologies for the synthesis of naturally occurring "peptaibol" antibiotics and conformationally designed analogs. In: Aubry A, Marraud M, Vitoux B (eds) Second Forum on Peptides 1989. Colloque INSERM/John Libbey Eurotext Ltd, vol 174, pp 251-255
    • (1989) Second Forum on Peptides 1989 , vol.174 , pp. 251-255
    • Brückner, H.1    Currle, M.2
  • 6
    • 0005923684 scopus 로고
    • Total synthesis of the peptaibol antibiotic trichovirin
    • Schneider CH, Eberle AN (eds) Peptides 1992. ESCOM, Leiden
    • nd European Peptide Symposium. ESCOM, Leiden, pp 385-386
    • (1992) nd European Peptide Symposium , pp. 385-386
    • Brückner, H.1    Koza, A.2
  • 7
    • 0021989947 scopus 로고
    • Trichotoxin A40. Purification by counter-current distribution and sequencing of isolated fragments
    • Brückner H, König WA, Aydin M, Jung G (1985) Trichotoxin A40. Purification by counter-current distribution and sequencing of isolated fragments. Biochim Biophys Acta 827: 51-62
    • (1985) Biochim Biophys Acta , vol.827 , pp. 51-62
    • Brückner, H.1    König, W.A.2    Aydin, M.3    Jung, G.4
  • 10
    • 0028200758 scopus 로고
    • Fungal metabolites. XIII. Isolation and structural elucidation of new peptaibols, trichodecenins-I and -II, from Trichoderma viride
    • Fujita T, Wada S, Iida A, Nishimura T, Kanai M, Toyama N (1994) Fungal metabolites. XIII. Isolation and structural elucidation of new peptaibols, trichodecenins-I and -II, from Trichoderma viride. Chem Pharm Bull 42/3: 489-494
    • (1994) Chem Pharm Bull , vol.42 , Issue.3 , pp. 489-494
    • Fujita, T.1    Wada, S.2    Iida, A.3    Nishimura, T.4    Kanai, M.5    Toyama, N.6
  • 11
    • 12444273428 scopus 로고
    • The crystal structures of two Aib-containing tripeptides
    • Gessmann R, Brückner H, Kokkinidis M (1993) The crystal structures of two Aib-containing tripeptides. Amino Acids 5: 108
    • (1993) Amino Acids , vol.5 , pp. 108
    • Gessmann, R.1    Brückner, H.2    Kokkinidis, M.3
  • 12
    • 0037508118 scopus 로고
    • The crystal structure of Z-Leu-Aib-Pro-Leuol, the synthetic, protected C-terminal tetrapeptide of trichovirin
    • Gessmann R, Kokkinidis M, Brückner H (1994) The crystal structure of Z-Leu-Aib-Pro-Leuol, the synthetic, protected C-terminal tetrapeptide of trichovirin. Z Kristallogr 209: 597-603
    • (1994) Z Kristallogr , vol.209 , pp. 597-603
    • Gessmann, R.1    Kokkinidis, M.2    Brückner, H.3
  • 13
    • 2442720652 scopus 로고    scopus 로고
    • The crystal structures of the synthetic C-terminal octa- and dodecapeptides of trichovirin
    • Gessmann R, Benos P, Brückner H, Kokkinidis M (1999) The crystal structures of the synthetic C-terminal octa- and dodecapeptides of trichovirin. J Peptide Sci 5: 83-95
    • (1999) J Peptide Sci , vol.5 , pp. 83-95
    • Gessmann, R.1    Benos, P.2    Brückner, H.3    Kokkinidis, M.4
  • 14
    • 0017577989 scopus 로고
    • Synthesis of a 19-residue peptide with alamethicin-like activity
    • Gisin BF, Kobayashi S, Hall JE (1977) Synthesis of a 19-residue peptide with alamethicin-like activity. Proc Natl Acad Sci USA 74: 115-119
    • (1977) Proc Natl Acad Sci USA , vol.74 , pp. 115-119
    • Gisin, B.F.1    Kobayashi, S.2    Hall, J.E.3
  • 15
    • 0028920495 scopus 로고
    • Fungal metabolites. XVIII. New membrane-modifying peptides, trichorozins I-IV, from the fungus Trichoderma harzianum
    • Iida A, Sanekata M, Wada S, Fujita T, Tanaka H, Enoki A, Fuse G, Kanai M, Asami K (1995) Fungal metabolites. XVIII. New membrane-modifying peptides, trichorozins I-IV, from the fungus Trichoderma harzianum. Chem Pharm Bull 43/3: 392-397
    • (1995) Chem Pharm Bull , vol.43 , Issue.3 , pp. 392-397
    • Iida, A.1    Sanekata, M.2    Wada, S.3    Fujita, T.4    Tanaka, H.5    Enoki, A.6    Fuse, G.7    Kanai, M.8    Asami, K.9
  • 16
    • 0345035375 scopus 로고    scopus 로고
    • Detection of new sequences of peptaibol antibiotics trichotoxins A-40 by on-line liquid chromatography-electrospray ionization mass spectrometry
    • Jaworski A, Brückner H (1999) Detection of new sequences of peptaibol antibiotics trichotoxins A-40 by on-line liquid chromatography-electrospray ionization mass spectrometry. J Chromatogr A 862: 179-189
    • (1999) J Chromatogr A , vol.862 , pp. 179-189
    • Jaworski, A.1    Brückner, H.2
  • 17
    • 1642618117 scopus 로고    scopus 로고
    • New sequences and new fungal producers of peptaibol antibiotics antiamoebins
    • Jaworski A, Brückner H (2000) New sequences and new fungal producers of peptaibol antibiotics antiamoebins. J Peptide Sci 6: 149-167
    • (2000) J Peptide Sci , vol.6 , pp. 149-167
    • Jaworski, A.1    Brückner, H.2
  • 18
    • 0034862003 scopus 로고    scopus 로고
    • Sequences of polypeptide antibiotics stilboflavins, natural peptaibol libraries of the mold Stilbella flavipes
    • Jaworski A, Brückner H (2001) Sequences of polypeptide antibiotics stilboflavins, natural peptaibol libraries of the mold Stilbella flavipes. J Peptide Sci 7: 433-447
    • (2001) J Peptide Sci , vol.7 , pp. 433-447
    • Jaworski, A.1    Brückner, H.2
  • 19
    • 0032767307 scopus 로고    scopus 로고
    • Structures of trichovirins II, peptaibol antibiotics from the mold Trichoderma viride NRRL 5243
    • Jaworski A, Kirschbaum J, Brückner H (1999) Structures of trichovirins II, peptaibol antibiotics from the mold Trichoderma viride NRRL 5243. J Peptide Sci 5: 341-351
    • (1999) J Peptide Sci , vol.5 , pp. 341-351
    • Jaworski, A.1    Kirschbaum, J.2    Brückner, H.3
  • 20
    • 0033838976 scopus 로고    scopus 로고
    • Synthesis of conformationally restricted cyclic hexadepsipeptides via direct amide cyclization
    • Koch KN, Heimgartner H (2000) Synthesis of conformationally restricted cyclic hexadepsipeptides via direct amide cyclization. Helv Chim Acta 83: 1881-1900
    • (2000) Helv Chim Acta , vol.83 , pp. 1881-1900
    • Koch, K.N.1    Heimgartner, H.2
  • 21
    • 0001947018 scopus 로고
    • Peptides-XI. Synthesis of peptides derived from alpha-methylalanine
    • Leplawy MT, Jones DS, Kenner GW, Sheppard RC (1960) Peptides-XI. Synthesis of peptides derived from alpha-methylalanine. Tetrahedron 11: 39-51
    • (1960) Tetrahedron , vol.11 , pp. 39-51
    • Leplawy, M.T.1    Jones, D.S.2    Kenner, G.W.3    Sheppard, R.C.4
  • 23
    • 0029875062 scopus 로고    scopus 로고
    • Ein neues 3-Amino-2H-azirin als Aib-Pro-Baustein: Synthese des C-terminalen Nonapeptides von Trichovirin I 1B
    • Luykx R, Bucher CB, Linden A, Heimgartner H (1996) Ein neues 3-Amino-2H-azirin als Aib-Pro-Baustein: Synthese des C-terminalen Nonapeptides von Trichovirin I 1B. Helv Chim Acta 79: 527-540
    • (1996) Helv Chim Acta , vol.79 , pp. 527-540
    • Luykx, R.1    Bucher, C.B.2    Linden, A.3    Heimgartner, H.4
  • 24
    • 0028277823 scopus 로고
    • Fungal metabolites. XVII. Synthesis and NMR study of ion channel-forming peptides, trichosporin B-VIa and its derivative
    • Nagaoka Y, Iida A, Fujita T (1994) Fungal metabolites. XVII. Synthesis and NMR study of ion channel-forming peptides, trichosporin B-VIa and its derivative. Chem Pharm Bull 42/6: 1258-1263
    • (1994) Chem Pharm Bull , vol.42 , Issue.6 , pp. 1258-1263
    • Nagaoka, Y.1    Iida, A.2    Fujita, T.3
  • 25
    • 0019519870 scopus 로고
    • Solution phase synthesis of alamethicin I
    • Nagaraj R, Balaram P (1981) Solution phase synthesis of alamethicin I. Tetrahedron 37: 1263-1270
    • (1981) Tetrahedron , vol.37 , pp. 1263-1270
    • Nagaraj, R.1    Balaram, P.2
  • 26
    • 0038183462 scopus 로고    scopus 로고
    • Synthesis of the isotopically labelled C-terminal fragment of zervamicin: An approach to the synthesis of Aib-containing peptides
    • Ogrel A, Bloemhoff W, Lugtenburg J, Raap J (1997) Synthesis of the isotopically labelled C-terminal fragment of zervamicin: an approach to the synthesis of Aib-containing peptides. Liebigs Ann/Recueil: 41-47
    • (1997) Liebigs Ann/Recueil , pp. 41-47
    • Ogrel, A.1    Bloemhoff, W.2    Lugtenburg, J.3    Raap, J.4
  • 27
    • 0032951149 scopus 로고    scopus 로고
    • Total synthesis and membrane modifying properties of the lipopeptaibol trikoningin KB II and its analogues with acyl chains of different length at the N- and C-termini
    • Piazza C, Formaggio F, Crisma M, Toniolo C, Kamphuis J, Kaptein B, Broxterman QB (1999) Total synthesis and membrane modifying properties of the lipopeptaibol trikoningin KB II and its analogues with acyl chains of different length at the N- and C-termini. J Peptide Sci 5: 96-102
    • (1999) J Peptide Sci , vol.5 , pp. 96-102
    • Piazza, C.1    Formaggio, F.2    Crisma, M.3    Toniolo, C.4    Kamphuis, J.5    Kaptein, B.6    Broxterman, Q.B.7
  • 28
    • 0002082310 scopus 로고    scopus 로고
    • The peptaibol antibiotics from Trichoderma soil fungi; structural diversity and membrane properties
    • Rebuffat S, Goulard C, Bodo B, Roquebert M-F (1999) The peptaibol antibiotics from Trichoderma soil fungi; structural diversity and membrane properties. Recent Res Devel Org Bioorg Chem 3: 65-91
    • (1999) Recent Res Devel Org Bioorg Chem , vol.3 , pp. 65-91
    • Rebuffat, S.1    Goulard, C.2    Bodo, B.3    Roquebert, M.-F.4
  • 29
    • 0021947255 scopus 로고
    • Total synthesis of the α-helical eicosapeptide antibiotic alamethicin
    • Schmitt H, Jung G (1985) Total synthesis of the α-helical eicosapeptide antibiotic alamethicin. Liebigs Ann Chem: 321-344
    • (1985) Liebigs Ann Chem , pp. 321-344
    • Schmitt, H.1    Jung, G.2
  • 34
    • 0000528761 scopus 로고
    • Fmoc amino acid fluorides: Convenient reagents for the solid-phase assembly of peptides incorporating sterically hindered residues
    • Wenschuh H, Beyermann M, Krause E, Brudel M, Winter R, Schümann M, Carpino LA, Bienert M (1994) Fmoc amino acid fluorides: convenient reagents for the solid-phase assembly of peptides incorporating sterically hindered residues. J Org Chem 59: 3275-3280
    • (1994) J Org Chem , vol.59 , pp. 3275-3280
    • Wenschuh, H.1    Beyermann, M.2    Krause, E.3    Brudel, M.4    Winter, R.5    Schümann, M.6    Carpino, L.A.7    Bienert, M.8
  • 35
    • 0028862474 scopus 로고
    • Stepwise automated solid phase synthesis of naturally occurring peptaibols using Fmoc amino acid fluorides
    • Wenschuh H, Beyermann M, Haber H, Seydel JK, Krause E, Bienert M (1995) Stepwise automated solid phase synthesis of naturally occurring peptaibols using Fmoc amino acid fluorides. J Org Chem 60: 405-419
    • (1995) J Org Chem , vol.60 , pp. 405-419
    • Wenschuh, H.1    Beyermann, M.2    Haber, H.3    Seydel, J.K.4    Krause, E.5    Bienert, M.6
  • 36
    • 0025319387 scopus 로고
    • 2. Synthesis of peptides containing α, α-disubstituted α-amino acids by the azirine/oxazolone method: The (12-20)-nonapeptide of the ionophore alamethicin
    • Wipf P, Heimgartner H (1990) 2. Synthesis of peptides containing α, α-disubstituted α-amino acids by the azirine/oxazolone method: the (12-20)-nonapeptide of the ionophore alamethicin. Helv Chim Acta 73: 13-24
    • (1990) Helv Chim Acta , vol.73 , pp. 13-24
    • Wipf, P.1    Heimgartner, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.