Optically active cyclic hexapeptides with covalently attached pyrene probes: Selective alkaline earth metal ion recognition using excimer emission

被引:38
作者
Strauss, J [1 ]
Daub, J [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany
关键词
D O I
10.1021/ol0170354
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The synthesis of two optically active pyrene-modified cyclic hexapetides and their selectivity toward the complexation of alkaline earth metal ions are reported. Complexation was studied by optical and chiroptical methods. The cyclic peptides are forming 2:1 sandwich complexes with the metal ions.
引用
收藏
页码:683 / 686
页数:4
相关论文
共 41 条
  • [11] A fluorescence assay for leucine zipper dimerization: Avoiding unintended consequences of fluorophore attachment
    Daugherty, DL
    Gellman, SH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) : 4325 - 4333
  • [12] Signaling recognition events with fluorescent sensors and switches
    de Silva, AP
    Gunaratne, HQN
    Gunnlaugsson, T
    Huxley, AJM
    McCoy, CP
    Rademacher, JT
    Rice, TE
    [J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1515 - 1566
  • [13] Synthesis of α- and β-carbon-linked serine analogues of the Pk trisaccharide
    Debenham, SD
    Cossrow, J
    Toone, EJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) : 9153 - 9163
  • [14] N-methylated cyclic RGD peptides as highly active and selective αvβ3 integrin antagonists
    Dechantsreiter, MA
    Planker, E
    Mathä, B
    Lohof, E
    Hölzemann, G
    Jonczyk, A
    Goodman, SL
    Kessler, H
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (16) : 3033 - 3040
  • [15] ONE-DIMENSIONAL AROMATIC CRYSTALS IN SOLUTION .4. GROUND-STATE AND EXCITED-STATE INTERACTIONS OF POLY(L-1-PYRENYLALANINE) STUDIED BY CHIROPTICAL SPECTROSCOPY INCLUDING CIRCULARLY POLARIZED FLUORESCENCE AND FLUORESCENCE-DETECTED CIRCULAR-DICHROISM
    EGUSA, S
    SISIDO, M
    IMANISHI, Y
    [J]. MACROMOLECULES, 1985, 18 (05) : 882 - 889
  • [16] 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
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8831 - 8838
  • [17] FORSTER T, 1955, Z ELEKTROCHEM, V59, P976
  • [18] SELF-ASSEMBLING ORGANIC NANOTUBES BASED ON A CYCLIC PEPTIDE ARCHITECTURE
    GHADIRI, MR
    GRANJA, JR
    MILLIGAN, RA
    MCREE, DE
    KHAZANOVICH, N
    [J]. NATURE, 1993, 366 (6453) : 324 - 327
  • [19] Haubner R., 1997, ANGEW CHEM, V109, P1440
  • [20] STRUCTURAL AND ENERGETIC PARAMETERS OF CA2+ BINDING TO PEPTIDES AND PROTEINS
    HORI, K
    KUSHICK, JN
    WEINSTEIN, H
    [J]. BIOPOLYMERS, 1988, 27 (12) : 1865 - 1886