Chemical Synthesis of the 12 kDa Human Myokine Irisin by α-Ketoacid-Hydroxylamine (KAHA) Ligation

被引:8
|
作者
Wucherpfennig, Thomas G. [1 ]
Mueller, Sebastian [2 ]
Wolfrum, Christian [2 ]
Bode, Jeffrey W. [1 ,3 ]
机构
[1] Swiss Fed Inst Technol, Dept Chem & Appl Biosci, Lab Organ Chem, CH-8093 Zurich, Switzerland
[2] Swiss Fed Inst Technol, Dept Hlth Sci & Technol, Lab Translat Nutr Biol, CH-8603 Schwerzenbach, Switzerland
[3] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
基金
瑞士国家科学基金会;
关键词
Proteins; Cytokines; Total synthesis; Metabolism; Ligation Reactions; PROTEIN-SYNTHESIS; 5-OXAPROLINE; PEPTIDES; GENE; FAT;
D O I
10.1002/hlca.201600160
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Irisin is a recently discovered protein hormone with a conserved sequence among vertebrates and with putative functions in the regulation of adipose tissue and bone metabolism. We report the first chemical synthesis using two sequential ketoacid-hydroxylamine (KAHA) ligations to give milligram quantities of unlabeled and fluorescence-labeled irisin protein. The synthetic proteins were utilized in cell binding assays, which indicated the expected binding characteristics to stromal cells of white adipose tissue. These studies strongly imply the presence of a specific irisin receptor and provide a path to its identification with synthetic irisin.
引用
收藏
页码:897 / 907
页数:11
相关论文
共 40 条
  • [1] α-Ketoacid-hydroxylamine (KAHA) ligation for the chemical synthesis of modifier proteins
    Ogunkoya, A. O.
    Pattabiraman, V. R.
    Bode, J. W.
    [J]. JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S192 - S192
  • [2] Chemical Synthesis of the 20kDa Heme Protein Nitrophorin4 by -Ketoacid-Hydroxylamine (KAHA) Ligation
    He, Chunmao
    Kulkarni, Sameer S.
    Thuaud, Frederic
    Bode, Jeffrey W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) : 12996 - 13001
  • [3] Protein chemical synthesis by α-ketoacid-hydroxylamine ligation
    Harmand, Thibault J.
    Murar, Claudia E.
    Bode, Jeffrey W.
    [J]. NATURE PROTOCOLS, 2016, 11 (06) : 1130 - 1147
  • [4] Chemical Protein Synthesis with the α-Ketoacid-Hydroxylamine Ligation
    Bode, Jeffrey W.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (09) : 2104 - 2115
  • [5] Chemical Protein Synthesis by Chemoselective α-Ketoacid-Hydroxylamine (KAHA) Ligations with 5-Oxaproline
    Pattabiraman, Vijaya R.
    Ogunkoya, Ayodele O.
    Bode, Jeffrey W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) : 5114 - 5118
  • [6] Improved synthesis of (S)-N-Boc-5-oxaproline for protein synthesis with the α-ketoacid-hydroxylamine (KAHA) ligation
    Murar, Claudia E.
    Harmand, Thibault J.
    Bode, Jeffrey W.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (18) : 4996 - 5001
  • [7] Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid-hydroxylamine (KAHA) ligation
    Rohrbacher, Florian
    Zwicky, Andre
    Bode, Jeffrey W.
    [J]. CHEMICAL SCIENCE, 2017, 8 (05) : 4051 - 4055
  • [8] Chemoselective a-ketoacid-hydroxylamine (KAHA) ligation with 5-oxaproline for chemical protein synthesis
    Pattabiraman, V. R.
    Ogunkoya, A. O.
    Bode, J. W.
    [J]. JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S24 - S24
  • [9] Facile folding of insulin variants bearing a prosthetic C-peptide prepared by -ketoacid-hydroxylamine (KAHA) ligation
    Boross, Gabor N.
    Shimura, Satomi
    Besenius, Melissa
    Tennagels, Norbert
    Rossen, Kai
    Wagner, Michael
    Bode, Jeffrey W.
    [J]. CHEMICAL SCIENCE, 2018, 9 (44) : 8388 - 8395
  • [10] Protein chemical synthesis by α-ketoacid–hydroxylamine ligation
    Thibault J Harmand
    Claudia E Murar
    Jeffrey W Bode
    [J]. Nature Protocols, 2016, 11 : 1130 - 1147