Fmoc-based chemical synthesis and selective binding to supercoiled DNA of the p53 C-terminal segment and its phosphorylated and acetylated derivatives

Journal of Peptide Science

Volumn 10, Issue 8, 2004, Pages 479-493

  Teruya, Kenta ^a   Murphy, Angela C ^a   Burlin, Tom ^b   Appella, Ettore ^a   Mazur, Sharlyn J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

Author keywords

p53 C terminal domain; Peptide thiolester condensation; Photolabile protecting group; Safety catch resin approach; Selective binding to supercoiled DNA

Indexed keywords

AMINO ACID; CARBONYL DERIVATIVE; DNA; PLASMID DNA; PROTEIN DERIVATIVE; PROTEIN P53; RESIN; SULFONAMIDE; SYNTHETIC PEPTIDE; THIOESTER;

ACETYLATION; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DNA SUPERCOILING; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTEIN DNA BINDING; PROTEIN DOMAIN; PROTEIN PHOSPHORYLATION; PROTEIN PROCESSING; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SOLID STATE;

ACETYLATION; AMINO ACIDS; BINDING, COMPETITIVE; DNA, SUPERHELICAL; FLUORENES; HUMANS; MOLECULAR SEQUENCE DATA; PEPTIDES; PHOSPHORYLATION; TUMOR SUPPRESSOR PROTEIN P53;

EID: 4444376263     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.552     Document Type: Article

References (48)

1. Hojo H, Aimoto S. Polypeptide synthesis using the S-alkyl thioester of a partially protected peptide segment. Synthesis of the DNA-binding domain of c-Myb protein (142-193)-NH2. Bull. Chem. Soc. Jpn 1991; 64: 111-117.
2. Aimoto S. Polypeptide synthesis by the thioester method. Biopolymers (Peptide Sci.) 1999; 51: 247-265.
3. Hojo H, Know Y, Kakuta Y, Tsuda S, Tanaka I, Hikichi K, Aimoto S. Development of a linker with an enhanced stability for the preparation of peptide thioesters and its application to the synthesis of a stable-isotope-labelled HU-type DNA binding protein. Bull. Chem. Soc. Jpn 1993; 66: 2700-2706.
4. Dawson PE, Muir TW, Clark-Lewis I, Kent SB. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-779.
5. Canne LE, Bark SJ, Kent SBH. Extending the applicability of native chemical ligation. J. Am. Chem. Soc. 1996; 118: 5891-5896.
6. Botti P, Carrasco MR, Kent SBH. Native chemical ligation using removable N-α-(1-phenyl-2-mercaptoethyl) auxiliaries. Tetrahedron Lett. 2001; 42: 1831-1833.
7. Kawakami T, Akaji K, Aimoto S. Peptide bond formation mediated by 4,5-dimethoxy-2-mercaptobenzylamine after periodate oxidation of the N-terminal serine residue. Org. Lett. 2001; 3: 1403-1405.
8. Nilsson BL, Kiessling LL, Raines RT. High-yielding Staudinger ligation of a phosphinothioester and azide to form a peptide. Org. Lett. 2001; 3: 9-12.
9. Futaki S, Sogawa K, Maruyama J, Asahara T, Niwa M, Hojo H. Preparation of peptide thioesters using Fmoc-solid-phase peptide synthesis and its application to the construction of a template-assembled synthetic protein (TASP). Tetrahedron Lett. 1997; 38: 6237-6240.
10. Li X, Kawakami T, Aimoto S. Direct preparation of peptide thioesters using an Fmoc solid-phase method. Tetrahedron Lett. 1998; 39: 8669-8672.
11. Ingenito R, Bianchi E, Fattori D, Pessi A. Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry. J. Am. Chem. Soc. 1999; 121: 11369-11374.
12. Alsina J, Yokum TS, Albericio F, Barany G. Back-bone amide linker (BAL) strategy for Nα-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters. J. Org. Chem. 1999; 64: 8761-8769.
13. Swinnen D, Hilvert D. Facile, Fmoc-compatible solid-phase synthesis of peptideC-termipal thioesters. Org. Lett. 2000; 2: 2439-2442.
14. Aimoto S. Contemporary methods for peptide and protein synthesis. Curr. Org. Chem. 2001; 5: 45-87.
15. Kawakami T, Hasegawa K, Aimoto S. Synthesit, of a phosphorylated polypeptide by a thioester method. Bull. Chem. Soc. Jpn 2000; 73: 197-203.
16. Mizuno M, Haneda K, Iguchi R, Muramoto I, Kawakami T, Aimoto S, Yamamoto K, Inazu T. Synthesis of a glycopeptide containing oligosaccharides: Chemoenzymatic synthesis of eel calcitonin analogues having natural N-linked oligosaccharides. J. Am. Chem. Soc. 1999; 121: 284-290.
17. Hasegawa K, Sha YL, Bang JK, Kawakami T, Akaji K, Aimoto S. Preparation of phosphopeptide thioesters by Fmoc- and Fmoc(2-F)-solid phase synthesis. Lett. Peptide Sci. 2002; 8: 277-284.
18. Lane DP. Cancer. p53, guardian of the genome. Nature 1992; 358: 15-16.
19. Albrechtsen N, Dornreiter I, Grosse F, Kim E, Wiesmüller L, Deppert W. Maintenance of genomic integrity by p53: complementary roles for activated and non-activated p53. Oncogene 1999; 18: 7706-7717.
20. Appella E, Anderson CW. Post-translational modifications and activation of p53 by genotoxic stresses. Eur. J. Biochem. 2001; 268: 2764-2772.
21. Pavletich NP, Chambers KA, Pabo CO. The DNA-binding domain of p53 contains the four conserved regions and the major mutation hot spots. Genes Dev. 1993; 7: 2556-2564.
22. El-Deiry WS, Kern SE, Pietenpol JA, KinzIer KW, Vogelstein B. Definition of a consensus binding-site for p53. Nature Genet. 1992; 1: 45-49.
23. Palecek E, Vlk D, Stankova V, Brazda V, Hupp TR, Schaper A, Jovin TM. Tumor suppressor protein p53 binds preferentially to supercoiled DNA. Oncogene 1997; 15: 2201-2209.
24. Mazur SJ, Sakaguchi K, Appella E, Wang XW, Harris CC, Bohr VA. Preferential binding of tumor suppressor p53 to positively or negatively supercoiled DNA involves the C-terminal domain. J. Mot. Biol. 1999; 22: 241-249.
25. Brazdova M, Palecek J, Cherny DI, Billova S, Fojta M, Pecinka P, Vojtesek B, Jovin TM, Palecek E. Role of tumor suppressor p53 domains in selective binding to supercoiled DNA. Nucleic Acids Res. 2002: 30: 4966-4974.
26. Sakamoto H, Kodama H, Higashimoto Y, Kondo M, Lewis MS, Anderson CW, Appella E, Sakaguchi K. Chemical synthesis of phosphorylated peptides of the carboxy-terminal domain of human p53 by a segment condensation method. Int. J. Peptide Protein Res. 1996; 48:429-442.
27. Amit B, Zehave U, Patchornik A. Photosensitive protecting groups of amino sugars and their use in glycoside synthesis. 2-Nitrobenzyloxycarbonylamino and 6-nitroveratryloxycarbonylamino derivatives. J. Org. Chem. 1974; 39: 192-196.
28. Itoh M, Hagiware D, Kamiya T. A new tertbutyloxycarbonylating reagent, 2-tert-butyloxycarbonyloxyimino-2-phenylacetonitrile. Tetrahedron Lett. 1975; 16: 4393-4394.
29. Ingenito R, Dreznjak D, Guffler S, Wenschuh H. Efficient loading of sulfonamide safety-catch linkers by Fmoc amino acid fluorides. Org. Lett. 2002; 4: 1187-1188.
30. Carpino AL, Sadat-Aalaee D, Chao HG, DeSelms RH. ((9-Fluorenylmethyl)oxy)carbonyI (Fmoc) amino acid fluorides. Convenient new peptide coupling reagents applicable to the Fmoc/tert-butyl strategy for solution and solid-phase synthesis. J. Am. Chem. Soc. 1990; 112: 9651-9652.
31. King DS, Fields CG, Fields GB. A cleavage method which minimized side reactions following Fmoc solid phase peptide synthesis. Int. J. Peptide Protein Res. 1990; 36: 255-266.
32. Wakamiya T, Togashi R, Nishida T, Saruta K, Yasuoka J, Kusumoto S. An efficient procedure for solid-phase synthesis of phosphopeptides by the Fmoc strategy. Chem. Lett. 1994; 1099-1102.
33. König W, Geiger R. Racemisierung bet peptidsynthesen. Chem. Ber. 1970; 103: 2024-2033.
34. Kawakami T, Kogure S, Aimoto S. Synthesis of cysteine-containing polypeptide using a peptide thioester in the presence of silver chloride as an activator. Bull. Chem. Soc. Jpn 1996; 69: 3331-3338.
35. Hofmann RM, Muir TW. Recent advances in the application of expressed protein ligation to protein engineering. Curr. Opin. Biotech. 2002; 13: 297-303.
36. Dawson PE, Kent SBH. Synthesis of native proteins by chemical ligation. Annu. Rev. Biochem. 2000; 69: 923-960.
37. Vizzavona J, Dick F, Vocherr T. Synthesis and application of an auxiliary group for chemical ligation at the X-Gly site. Bioorg. Med. Chem. Lett. 2002; 12: 1963-1965.
38. Offer J, Boddy CNC, Dawson PE. Extending synthetic access to proteins with a removable acyl transfer auxiliary. J. Am. Chem. Soc. 2002; 124: 4642-4646.
39. Utas EA, Perich JW, Tregear GW, Johns RB. Synthesis of 0-phosphotyrosine-containing peptides. 3. Synthesis of H-Pro-Tyr(P)-Val-OH via dimethylphosphate protection and the use of improved deprotection procedures. J. Org. Chem. 1990; 55: 4181-4187.
40. Teruya K, Kawakami T, Akaji K, Aimoto S. Total synthesis of [L401, C90A, C109A]-human T-cell leukemia virus-type 1 protease. Tetrahedron Lett. 2002; 43: 1487-1490.
41. Chene P. The role of tetramerization in p53 function. Oncogene 2001; 20: 2611-2617.
42. Mateu GM, Fercht RA. Nine hydrophobic side chains are key determinants of the thermodynamic stability and oligornerization status of tumor suppressor p53 tetramerization domain. EMBO J. 1998; 17: 2748-2758.
43. Davison TS, Nie X, Ma W, Lin Y, Kay C: Benchimol S, Arrowsmith CH. Structure and functionality of a designed p53 dimer. J. Mot. Biol. 2001; 307: 605-617.
44. Larsen BD, Holm A. Incomplete Fmoc deprotection in solid-phase synthesis of peptides. Int. J. Peptide Protein Res. 1994; 17: 273-274.
45. Kaiser E, Colescott RL, Bossing CD, Cook PI. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970; 34: 595-598.
46. Flavell RR, Huse M, Goger M, Trester-Zedlitz M, KuriyanJ, Muir TW. Efficient semisynthesis of a tetraphosphorylated analogue of the type I TGFβreceptor. Org. Lett. 2002; 4: 165-168.
47. Brik A, Keinan E, Dawson PE. Protein synthesis by solid-phase chemical ligation using a safety catch linker. J. Org. Chem. 2000; 65: 3829-3835.
48. Kawakami T, Aimoto S. A photoremovable ligation auxiliary for use in polypeptide synthesis. Tetrahedron Lett. 2003; 44: 6059-6061.