N-terminal labeling of proteins by the Pictet-Spengler reaction

被引:39
作者
Sasaki, Tsubasa [1 ]
Kodama, Koichiro [1 ]
Suzuki, Hiroaki [1 ]
Fukuzawa, Seketsu [1 ]
Tachibana, Kazuo [1 ]
机构
[1] Univ Tokyo, Dept Chem, Sch Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
Pictet-Spengler reaction; myoglobin N-terminal; biotin; transamination reaction; keto aldehyde;
D O I
10.1016/j.bmcl.2008.07.033
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The Pictet-Spengler reaction was applied to the N-terminal labeling of horse heart myoglobin. This was performed in the following two steps: (1) conversion of the N-terminal glycine residue to an alpha-keto aldehyde by a transamination reaction and (2) condensation of the resulting activated myoglobin with tryptamine analogues by the Pictet-Spengler reaction. Ultraviolet (UV)/visible (vis) absorption and circular dichroism (CD) spectral data revealed that the tertiary structure of myoglobin was not altered by the Pictet-Spengler reaction. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4550 / 4553
页数:4
相关论文
共 17 条
[1]   Introducing genetically encoded aldehydes into proteins [J].
Carrico, Isaac S. ;
Carlson, Brian L. ;
Bertozzi, Carolyn R. .
NATURE CHEMICAL BIOLOGY, 2007, 3 (06) :321-322
[2]   Diels-Alder ligation of peptides and proteins [J].
de Araujo, Aline Dantas ;
Palomo, Jose M. ;
Cramer, Janina ;
Seitz, Oliver ;
Alexandrov, Kirill ;
Waldmann, Herbert .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) :6095-6109
[3]   N-terminal protein modification through a biomimetic transamination reaction [J].
Gilmore, Joshua M. ;
Scheck, Rebecca A. ;
Esser-Kahn, Aaron P. ;
Joshi, Neel S. ;
Francis, Matthew B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (32) :5307-5311
[4]   A HYDROPHILIC TETRAHYDRO-BETA-CARBOLINE IN HUMAN URINE [J].
HORIUCHI, K ;
YONEKAWA, O ;
IWAHARA, K ;
KANNO, T ;
KURIHARA, T ;
FUJISE, Y .
JOURNAL OF BIOCHEMISTRY, 1994, 115 (02) :362-366
[5]   Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation [J].
Kiick, KL ;
Saxon, E ;
Tirrell, DA ;
Bertozzi, CR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (01) :19-24
[6]   Regioselective carbon-carbon bond formation in proteins with palladium catalysis; New protein chemistry by organometallic chemistry [J].
Kodama, K ;
Fukuzawa, S ;
Nakayama, H ;
Kigawa, T ;
Sakamoto, K ;
Yabuki, T ;
Matsuda, N ;
Shirouzu, M ;
Takio, K ;
Tachibana, K ;
Yokoyama, S .
CHEMBIOCHEM, 2006, 7 (01) :134-139
[7]   Site-specific functionalization of proteins by organopalladium reactions [J].
Kodama, Koichiro ;
Fukuzawa, Seketsu ;
Nakayama, Hiroshi ;
Sakamoto, Kensaku ;
Kigawa, Takanori ;
Yabuki, Takashi ;
Matsuda, Natsuko ;
Shirouzu, Mikako ;
Takio, Koji ;
Yokoyama, Shigeyuki ;
Tachibana, Kazuo .
CHEMBIOCHEM, 2007, 8 (02) :232-238
[8]   Oxidative modification of proteins during aging [J].
Levine, RL ;
Stadtman, ER .
EXPERIMENTAL GERONTOLOGY, 2001, 36 (09) :1495-1502
[9]   A new ligation method for N-terminal tryptophan-containing peptides using the Pictet-Spengler reaction [J].
Li, XF ;
Zhang, LS ;
Hall, SE ;
Tam, JP .
TETRAHEDRON LETTERS, 2000, 41 (21) :4069-4073
[10]   Efficient N-terminal glycoconjugation of proteins by the N-end rule [J].
Merkel, Lars ;
Beckmann, Henning S. G. ;
Wittmann, Valentin ;
Budisa, Nediljko .
CHEMBIOCHEM, 2008, 9 (08) :1220-1224