Synthesis of photoswitchable amino acids based on azobenzene chromophores: building blocks with potential for photoresponsive biomaterials

被引:22
作者
Juodaityte, J [1 ]
Sewald, N [1 ]
机构
[1] Univ Bielefeld, Dept Chem, D-33501 Bielefeld, Germany
关键词
amino acid; photochemistry; peptide; azobenzene;
D O I
10.1016/j.jbiotec.2004.03.017
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Three novel derivatives of azobenzene substituted amino acids have been synthesized. The compounds may serve as photoswitchable building blocks in the synthesis of bicyclic peptides or peptide strands interconnected with a photoisomerizable group. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:127 / 138
页数:12
相关论文
共 22 条
[1]   meta-Aminoazobenzene as a thermo-insensitive photo-regulator of DNA-duplex formation [J].
Asanuma, H ;
Liang, XG ;
Komiyama, M .
TETRAHEDRON LETTERS, 2000, 41 (07) :1055-1058
[2]   TOTAL SYNTHESIS OF CRYPTOPHYCINS - REVISION OF THE STRUCTURES OF CRYPTOPHYCIN-A AND CRYPTOPHYCIN-C [J].
BARROW, RA ;
HEMSCHEIDT, T ;
LIANG, J ;
PAIK, S ;
MOORE, RE ;
TIUS, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (09) :2479-2490
[3]  
Behrendt R, 1999, J PEPT SCI, V5, P519, DOI 10.1002/(SICI)1099-1387(199911)5:11<519::AID-PSC223>3.0.CO
[4]  
2-3
[5]   Development of a solution-phase synthesis of minor groove binding bis-intercalators based on triostin A suitable for combinatorial synthesis [J].
Boger, DL ;
Lee, JK .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5996-6000
[6]   Synthesis of aryl nitroso derivatives by tert-butyl hypochlorite oxidation in homogeneous media.: Intermediates for the preparation of high-hyperpolarizability chromophore skeletons [J].
Davey, MH ;
Lee, VY ;
Miller, RD ;
Marks, TJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4976-4979
[7]   RAPID CATALYTIC TRANSFER REDUCTION OF AROMATIC NITRO-COMPOUNDS TO HYDROXYLAMINES [J].
ENTWISTLE, ID ;
GILKERSON, T ;
JOHNSTONE, RAW ;
TELFORD, RP .
TETRAHEDRON, 1978, 34 (02) :213-215
[8]   CONFORMATIONAL ASPECTS OF POLYPEPTIDE STRUCTURE .19. AZOAROMATIC SIDE-CHAIN EFFECTS [J].
GOODMAN, M ;
KOSSOY, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (21) :5010-&
[9]   Synthesis and photophysical properties of 3-[2-(pyridyl)benzoxazol-5-yl]-L-alanine derivatives [J].
Guzow, K ;
Szabelski, M ;
Malicka, J ;
Karolczak, J ;
Wiczk, W .
TETRAHEDRON, 2002, 58 (11) :2201-2209
[10]   Efficient synthesis of selectively protected L-Dopa derivatives from L-tyrosine via Reimer-Tiemann and Dakin reactions [J].
Jung, ME ;
Lazarova, TI .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1553-1555