The Central Dogma of molecular biology and an expanded proteome
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1 The Central Dogma of molecular biology and an expanded proteome 2016 Thermo Fisher Scientific Inc., verview of Post-Translational Modifications (PTMs) Ref: 12/1/16 1
2 Posttranslational modifications (PTMs) 31/11/16 2
3 PTMs of proteins: regulation of protein function The human proteome is highly dynamic and changes in response to various stimuli. Posttranslational modifications help to regulate the necessary cellular activities. W. P. Heal, E. W. Tate, rg. Biomol. Chem. 2010, 8, /1/16 3
4 PTMs of chromatin histone modifications, transcriptional control, epigenetics methylation (Lys, Arg) acetylation (Lys) phosphorylation (Ser, Thr, Tyr) ubiquitination (Lys) P. Jones, MedChemComm 2012, 3, /1/16 4
5 An expanded Central Dogma of molecular biology: posttranslational modifications William Reusch, Virtual Textbook of rganic Chemistry Ref: 12/1/16 5
6 Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B., Science. 1994, 266, /1/16 6
7 Anaïs F. M. Noisier and Fernando Albericio, Advance in ligation techniques for peptide and protein synthesis, in Amino Acids, Peptides and Proteins: Volume 39, 2014, 39, pp /1/16 7
8 Isopeptide ligations with proteins via NCL Ubiquitin-mediated protein degradation Functions of ubiquitination (ubiquitylation): Antigen processing Apoptosis Biogenesis of organelles Cell cycle and division DNA transcription and repair Differentiation and development Immune response and inflammation Neural and muscular degeneration Modulation of cell surface receptors, ion channels and secretory pathway Response to stress Ribosome biogenesis Viral infection Nobel Prize in Chemistry, Ciechanover, Hershko, Rose 12/1/16 8
9 Isopeptide ligations with proteins via NCL K. S. Ajish Kumar, M. Haj-Yahya, D. lschewski, H. A. Lashuel and A. Brik, Angew. Chem., Int. Ed., 2009, 48, /1/16 9
10 Diversity of the Staudinger reaction Ph Ph P Ph + N N N R 2 R 1 N N Ph Ph P N Ph phosphazide R 1 R 2 N Ph 3 P N N R 2 R 1 N 2 Ph 3 P N R 2 R 1 Ph 3 P N R 2 R 1 H 2 Ph 3 P + H 2 N R 2 R 1 iminophosphorane R 1 R 2 N N diazo preparation R 1 N H R 2 Staudinger ligation 12/1/16 10
11 Diversity of the Staudinger reaction P N P N 2 H 3 B P S P S R Myers, E.L.; Raines, R.T., Angew. Chem. Int. Ed. 2009, 48, Chou, HH; Raines, R.T., J. Am. Chem. Soc. 2013, 135, Nilsson, B.L.; Kiessling, L.L.; Raines, R.T., rg. Lett. 2001, 3, Soellner, M.B.; Nilsson, B.L.; Raines, R.T., J. rg. Chem. 2002, 67, Tam, A.; Soellner, M.B.; Raines, R.T., J. Am. Chem. Soc. 2007, 129, /1/16 11 H N H N
12 Ligations with proteins via Staudinger and NCL: Total synthesis of active Rnase A Nilsson, B.L; Hondal, R.J; Soellner, M.B; and Raines, R.T, J. Am. Chem. Soc. 2002, 125, /1/16 12
13 Synthesis of DiUbiquitin via the Raines Traceless Staudinger ligation N 3 Andersen, K.A., Raines, R.T. 2015, Methods Mol Biol. 1248, /1/16 13
14 Chemoselective peptide macrocyclizations via the Traceless Staudinger ligation Kleineweischede, R.; Hackenberger, C.P.R., Angew. Chem. Int. Ed. 2008, 47, White, C.J.; Yudin, A.K. Nature Chem. 2011, 3, /1/16 14
15 Chalker, J.M.; Bernardes, G.J.L.; Lin, Y.A.; Davis, B.G., Chem. Asian J., 2009, 4, /11/16 15
16 Transient PTMs of side-chain functional groups phosphorylations Chen, Z.; Cole, P.A., Curr. pin. Chem. Biol., 2015, 28, /1/16 16
17 Transient PTMs of side-chain functional groups phosphorylations Bertran-Vicente, J.; Schümann, M., Hackenberger, C.P.R.; Krause, E., Anal. Chem. 2015, 87, /1/16 17
18 Chemoselective methods to investigate labile side-chain PTMs R. Serwa, I. Wilkening, G. Del Signore, M. Muhlberg, I. Claussnitzer, C. Weise, M. Gerrits and C. P. R. Hackenberger, Angew. Chem., Int. Ed., 2009, 48, I. Wilkening, G. del Signore and C. P. R. Hackenberger, Chem. Commun., 2008, /1/16 18
19 Synthetic and semi-synthetic methods to investigate labile side-chain PTMs R. Serwa, I. Wilkening, G. Del Signore, M. Muhlberg, I. Claussnitzer, C. Weise, M. Gerrits,; C. P. R. Hackenberger, Angew. Chem., Int. Ed., 2009, 48, Bertran-Vicente, J.; Serwa, R.A.; Schümann, M.; Schmieder, P.; Krause, E.; Hackenberger, C.P.R.; J. Am. Chem. Soc. 2014, 136, /1/16 19
20 Synthetic methods to investigate labile side-chain PTMs Bertran-Vicente, J.; Serwa, R.A.; Schümann, M.; Schmieder, P.; Krause, E.; Hackenberger, C.P.R.; J. Am. Chem. Soc. 2014, 136, /1/16 20
21 Synthetic methods to investigate labile side-chain PTMs Bertran-Vicente, J.; Penkert, M.; Nieto-Garcia,.; Jeckelmann, J.-M.; Schmieder, P.; Krause, E.; Hackenberger, C.P.R., Nature Comm. 2016, 7, Article number: Buchowiecka, A. K, Analyst, 2014, 139, /1/16 21
22 Synthetic methods to investigate labile side-chain PTMs Bertran-Vicente, J.; Penkert, M.; Nieto-Garcia,.; Jeckelmann, J.-M.; Schmieder, P.; Krause, E.; Hackenberger, C.P.R., Nature Comm. 2016, 7, Article number: /1/16 22
23 Nisin, from Lactobacillus sp.
24 SPPS with dehydroalanine Levengood, M.R.; van der Donk, W.A., Nat. Protoc., 2007, 1, /1/16 24
25 Chalker, J.M.; Bernardes, G.J.L.; Lin, Y.A.; Davis, B.G., Chem. Asian J., 2009, 4, /1/16 25
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