Synthesis of protein kinase Cδ C1b domain by native chemical ligation methodology and characterization of its folding and ligand binding

Journal of Peptide Science

Volumn 15, Issue 10, 2009, Pages 642-646

  Ohashi, Nami ^a   Nomura, Wataru ^a   Kato, Mai ^a   Narumi, Tetsuo ^a   Lewin, Nancy E ^b   Blumberg, Peter M ^b   Tamamura, Hirokazu ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

C1b domain; Ligand binding; Native chemical ligation; Protein kinase C

Indexed keywords

BIOTIN; DIACYLGLYCEROL; FLUORESCENT DYE; PHORBOL ESTER; PROTEIN KINASE C DELTA;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CONTROLLED STUDY; ENZYME MODIFICATION; ENZYME PHOSPHORYLATION; ENZYME SYNTHESIS; LIGAND BINDING; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN FOLDING; REACTION ANALYSIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; LIGANDS; PEPTIDE FRAGMENTS; PROTEIN BINDING; PROTEIN FOLDING; PROTEIN KINASE C-DELTA; PROTEIN STRUCTURE, TERTIARY;

EID: 70449641245     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1161     Document Type: Article

References (22)

1. Nishizuka Y. Intracellular signaling by hydrolysis of phospholipids and activation of protein kinase C. Science 1992; 11: 607-614.
2. Newton AC. Protein kinase C: structure, function, and regulation. J. Biol. Chem. 1995; 270: 28495-28498.
3. Watanabe T, Ono Y, Taniyama Y, Hazama K, Igarashi K, Ogita K, Kikkawa U, Nishizuka Y. Cell division arrest induced by phorbol ester in CHO cells overexpressing protein kinase C-delta subspecies. Proc. Natl Acad. Sci. USA 1992; 89: 10159-10163.
4. Mischak H, Pierce JH, Goodnight J, Kazanietz G, Blumberg PM, Mushinski JF. Phorbol ester-induced myeloid differentiation is mediated by protein kinase C-alpha and -delta and not by protein kinase C-beta II, -epsilon, -zeta, and -eta. J. Biol. Chem. 1993; 268: 20110-20115. (Pubitemid 23278909)
5. Li C, Wernig E, Leitges M, Hu Y, Xu Q. Mechanical stress-activated PKCδ regulates smooth muscle cell migration. FASEB J. 2003; 17: 2106-2108.
6. Ghayur T, Hugunin M, Talanian V, Ratnofsky S, Quinlan C, Emoto Y, Pandey P, Datta R, Huang Y, Kharbanda S, Allen H, Kamen R, Wong W, Kufe D. Proteolytic activation of protein kinase C delta by an ICE/CED 3-like protease induces characteristics of apoptosis. J. Exp. Med. 1996; 184: 2399-2404. (Pubitemid 27023739)
7. Humphries MJ, Limesand KH, Schneider JC, Nakayama KI, Anderson SM, Reyland ME. Suppression of apoptosis in the protein kinase Cδ null mouse in vivo. J. Biol. Chem. 2006; 281: 9728-9737.
8. Tamamura H, Sigano DM, Lewin NE, Blumberg PM, Marquez VE. Conformationally constrained analogues of diacylglycerol. 20. The search for an elusive binding site on protein kinase C through relocation of the carbonyl pharmacophore along the sn-1 side chain of 1,2-diacylglycerol lactones. J. Med. Chem. 2004; 47: 644-655. (Pubitemid 38129721)
9. Tamamura H, Sigano DM, Lewin NE, Peach ML, Nicklaus MC, Blumberg PM, Marquez VE. Conformationally constrained analogues of diacylglycerol (DAG). 23. Hydrophobic ligand-protein interactions versus ligand-lipid interactions of DAG-lactones with protein kinase C (PK-C). J. Med. Chem. 2004; 47: 4858-4864. (Pubitemid 39238260)
10. Marquez VE, Blumberg PM. Synthetic diacylglycerols (DAG) and DAG-lactones as activators of protein kinase C (PK-C). Acc. Chem. Res. 2003; 36: 434-443.
11. Irie K, Oie K, Nakahara A, Yanai Y, Ohigashi H, Wender PA, Fukuda H, Konishi H, Kikkawa U. Molecular basis for protein kinase C isozyme-selective binding: the synthesis, folding, and phorbol ester binding of the cysteine-rich domains of all protein kinase C isozymes. J. Am. Chem. Soc. 1998; 120: 9159-9167. (Pubitemid 28452689)
12. Dawson PE, Muir TW, Clark-Lewis I, Kent SBH. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-779. (Pubitemid 24359280)
13. Dawson PE, Churchill MJ, Ghadiri MR, Kent SBH. Modulation of reactivity in native chemical ligation through the use of thiol additives. J. Am. Chem. Soc. 1997; 119: 4325-4329.
14. αthioester formation using standard Fmoc-chemistry. Tetrahedron Lett. 2003; 44: 3551-3554.
15. Sharkey NA, Blumberg PM. Highly lipophilic phorbol esters as inhibitors of specific [3H]phorbol 12,13-dibutyrate binding. Cancer Res. 1985; 45: 19-24.
16. Kazanietz MG, Krausz KW, Blumberg PM. Differential irreversible insertion of protein kinase C into phospholipid vesicles by phorbol esters and related activators. J. Biol. Chem. 1992; 267: 20878-20886.
17. Kajihara Y, Yoshihara A, Hirano K, Yamamoto N. Convenient synthesis of a sialylglycopeptide-thioester having an intact and homogeneous complex-type disialyl-oligosaccharide. Carbohydr. Res. 2006; 341: 1333-1340. (Pubitemid 43795409)
18. Futaki S, Tatsuto K, Shiraishi Y, Sugiura Y. Total synthesis of artificial zinc-finger protein. Problems and perspectives. Biopolymers 2004; 76: 98-109. (Pubitemid 38529425)
19. Hackeng TM, Griffin JH, Dawson PE. Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology. Proc. Natl Acad. Sci. USA 1999; 96: 10068-10073.
20. Zhang G, Kazanietz MG, Blumberg PM, Hurley JH. Crystal structure of the cys2 activator-binding domain of protein kinase C delta in complex with phorbol ester. Cell 1995; 81: 917-924.
21. Tamamura H, Otaka T, Murakami T, Ibuka T, Sakano K, Waki M, Matsumoto A, Yamamoto N, Fujii N. An anti-HIV peptide, T22, forms a highly active complex with Zn(II). Biochem. Biophys. Res. Commun. 1996; 229: 648-652. (Pubitemid 27029085)
22. Kazanietz MG, Wang S, Milne GW, Lewin NE, Liu LH, Blumberg PM. Residues in the second cysteine-rich region of protein kinase C δ relevant to phorbol ester binding as revealed by site-directed mutagenesis. J. Biol. Chem. 1995; 270: 21852-21859.