Protein chemical synthesis by serine and threonine ligation

Proceedings of the National Academy of Sciences of the United States of America

Volumn 110, Issue 17, 2013, Pages 6657-6662

  Zhang, Yinfeng ^a   Xu, Ci ^a   Lam, Hiu Yung ^a   Lee, Chi Lung ^a   Li, Xuechen ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Acyl transfer; Chemoselective ligation; Synthetic protein

Indexed keywords

ACYLPHOSPHATASE; ERYTHROCYTE ACYLPHOSPHATASE; OVINE CORTICOLIBERIN; PARATHYROID HORMONE[1-34]; PEPTIDE DERIVATIVE; SALICYLALDEHYDE; SERINE; THREONINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; COMPLEX FORMATION; DEPROTECTION REACTION; ENZYME ACTIVITY; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEIN PROCESSING; PROTEIN STRUCTURE;

ACID ANHYDRIDE HYDROLASES; ALDEHYDES; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CORTICOTROPIN-RELEASING HORMONE; HUMANS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PEPTIDES; PROTEIN ENGINEERING; SERINE; SHEEP; TERIPARATIDE; THREONINE;

OVIS;

EID: 84876876557     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1221012110     Document Type: Article

References (48)

1. Kent SBH (2009) Total chemical synthesis of proteins. Chem Soc Rev 38(2):338-351.
2. Muralidharan V, Muir TW (2006) Protein ligation: An enabling technology for the biophysical analysis of proteins. Nat Methods 3(6):429-438.
3. Nilsson BL, Soellner MB, Raines RT (2005) Chemical synthesis of proteins. Annu Rev Biophys Biomol Struct 34:91-118.
4. Gamblin DP, Scanlan EM, Davis BG (2009) Glycoprotein synthesis: An update. Chem Rev 109(1):131-163.
5. Payne RJ, Wong CH (2010) Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins. Chem Commun (Camb) 46(1):21-43.
6. Yamamoto N, Tanabe Y, Okamoto R, Dawson PE, Kajihara Y (2008) Chemical synthesis of a glycoprotein having an intact human complex-type sialyloligosaccharide under the Boc and Fmoc synthetic strategies. J Am Chem Soc 130(2):501-510.
7. Nagorny P, et al. (2009) Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. Synthesis of beta-hFSH with chitobiose units at the natural linkage sites. J Am Chem Soc 131(16):5792-5799.
8. Tarrant MK, et al. (2012) Regulation of CK2 by phosphorylation and O-GlcNAcylation revealed by semisynthesis. Nat Chem Biol 8(3):262-269.
9. Sakamoto I, et al. (2012) Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo. J Am Chem Soc 134(12): 5428-5431.
10. Wilkinson BL, et al. (2012) Total synthesis of homogeneous antifreeze glycopeptides and glycoproteins. Angew Chem Int Ed Engl 51(15):3606-3610.
11. Wang P, et al. (2012) At last: Erythropoietin as a single glycoform. Angew Chem Int Ed Engl 51(46):11576-11584.
12. Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85(14):2149-2154.
13. Dawson PE, Muir TW, Clark-Lewis I, Kent SBH (1994) Synthesis of proteins by native chemical ligation. Science 266(5186):776-779.
14. Liu CF, Tam JP (1994) Peptide segment ligation strategy without use of protecting groups. Proc Natl Acad Sci USA 91(14):6584-6588.
15. Pattabiraman VR, Bode JW (2011) Rethinking amide bond synthesis. Nature 480(7378): 471-479.
16. Hackenberger CPR, Schwarzer D (2008) Chemoselective ligation and modification strategies for peptides and proteins. Angew Chem Int Ed Engl 47(52):10030-10074.
17. Kemp DS (1981) The amine capture strategy for peptide bond formation-an outline of progress. Biopolymers 20(9):1793-1804.
18. Kemp DS, Galakatos NG (1986) Peptide synthesis by prior thiol capture. 1. A convenient synthesis of 4-hydroxy-6-mercaptodibenzofuran and novel solid-phase synthesis of peptide-derived 4-(acyloxy)-6-mercaptodibenzofurans. J Org Chem 51(10):1821-1829.
19. Kemp DS, Galakatos NG, Bowen B, Tan K (1986) Peptide synthesis by prior thiol capture. 2. Design of templates for intramolecular O, N-acyl transfer. 4, 6-Disubstituted dibenzofurans as optimal spacing elements. J Org Chem 51(10):1829-1838.
20. McBride BJ, Kemp DS (1987) Peptide synthesis by prior thiol capture.. III. Assessment of levels of racemization during two typical thiol capture coupling reactions. Tetrahedron Lett 28(30):3435-3438.
21. Kemp DS, et al. (1986) Peptide synthesis by prior thiol capture. 4. Amide bond formation: the effect of a side-chain substituent on the rates of intramolecular O, N-acyl transfer. J Org Chem 51(17):3320-3324.
22. Kemp DS, Carey RI (1993) Synthesis of a 39-peptide and a 25-peptide by thiol capture ligations: Observation of a 40-fold rate acceleration of the intramolecular O, N-acyl-transfer reaction between peptide fragments bearing only cysteine protective groups. J Org Chem 58(8):2216-2222.
23. Yan LZ, Dawson PE (2001) Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization. J Am Chem Soc 123(4): 526-533.
24. Wan Q, Danishefsky SJ (2007) Free-radical-based, specific desulfurization of cysteine: A powerful advance in the synthesis of polypeptides and glycopolypeptides. Angew Chem Int Ed Engl 46(48):9248-9252.
25. Shang S, Tan Z, Danishefsky SJ (2011) Application of the logic of cysteine-free native chemical ligation to the synthesis of Human Parathyroid Hormone (hPTH). Proc Natl Acad Sci USA 108(15):5986-5989.
26. Wong CTT, Tung CL, Li X (2013) Synthetic cysteine surrogates used in native chemical ligation. Mol Biosyst, 10.1039/C2MB25437A.
27. Nilsson BL, Kiessling LL, Raines RT (2000) Staudinger ligation: A peptide from a thioester and azide. Org Lett 2(13):1939-1941.
28. Soellner MB, Nilsson BL, Raines RT (2006) Reaction mechanism and kinetics of the traceless Staudinger ligation. J Am Chem Soc 128(27):8820-8828.
29. Bode JW, Fox RM, Baucom KD (2006) Chemoselective amide ligations by decarboxylative condensations of N-alkylhydroxylamines and α-ketoacids. Angew Chem Int Ed Engl 45(8):1248-1252.
30. Pattabiraman VR, Ogunkoya AO, Bode JW (2012) Chemical protein synthesis by chemoselective α-ketoacid-hydroxylamine (KAHA) ligations with 5-oxaproline. Angew Chem Int Ed Engl 51(21):5114-5118.
31. Thomas GL, Payne RJ (2009) Phosphate-assisted peptide ligation. Chem Commun (Camb) 28(28):4260-4262.
32. Shangguan N, Katukojvala S, Greenberg R, Williams LJ (2003) The reaction of thio acids with azides: A new mechanism and new synthetic applications. J Am Chem Soc 125(26):7754-7755.
33. Crich D, Sana K, Guo S (2007) Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2, 4- dinitrobenzenesulfonamides. Org Lett 9(22): 4423-4426.
34. Wu X, Hu L (2007) Efficient amidation from carboxylic acids and azides via seleno-carboxylates: Application to the coupling of amino acids and peptides with azides. J Org Chem 72(3):765-774.
35. Kemp DS, Vellaccio F, Jr. (1975) Rapid intramolecular acyl transfer from phenol to carbinolamine-progress toward a new class of peptide coupling reagent. J Org Chem 40(20):3003-3004.
36. Kemp DS, Grattan JA, Reczek J (1975) Letter: Peptide bond formation by the amine capture principle. J Org Chem 40(23):3465-3466.
37. Chen G, et al. (2006) Studies related to the relative thermodynamic stability of C-terminal peptidyl esters of O-hydroxy thiophenol: Emergence of a doable strategy for non-cysteine ligation applicable to the chemical synthesis of glycopeptides. J Am Chem Soc 128(23):7460-7462.
38. Liu CF, Tam JP (1994) Chemical ligation approach to form a peptide bond between unprotected peptide segments. Concept and model study. J Am Chem Soc 116(10):4149-4153.
39. Tam JP, Miao Z (1999) Stereospecific pseudoproline ligation of N-terminal serine, threonine, or cysteine-containing unprotected peptides. J Am Chem Soc 121(39): 9013-9022.
40. Li X, Lam HY, Zhang Y, Chan CK (2010) Salicylaldehyde ester-induced chemoselective peptide ligations: Enabling generation of natural peptidic linkages at the serine/threonine sites. Org Lett 12(8):1724-1727.
41. Mende F, Seitz O (2011) 9-Fluorenylmethoxycarbonyl-based solid-phase synthesis of peptide α-thioesters. Angew Chem Int Ed Engl 50(6):1232-1240.
42. Blanco-Canosa JB, Dawson PE (2008) An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation. Angew Chem Int Ed Engl 47(36):6851-6855.
43. Gross CM, Lelièvre D, Woodward CK, Barany G (2005) Preparation of protected peptidyl thioester intermediates for native chemical ligation by Nalpha-9-fluorenylmethoxycarbonyl (Fmoc) chemistry: Considerations of side-chain and backbone anchoring strategies, and compatible protection for N-terminal cysteine. J Pept Res 65(3):395-410.
44. Vale W, Spiess J, Rivier C, Rivier J (1981) Characterization of a 41-residue ovine hypothalamic peptide that stimulates secretion of corticotropin and beta-endorphin. Science 213(4514):1394-1397.
45. Saag KG, et al. (2007) Teriparatide or alendronate in glucocorticoid-induced osteoporosis. N Engl J Med 357(20):2028-2039.
46. Stefani M, Taddei N, Ramponi G (1997) Insights into acylphosphatase structure and catalytic mechanism. Cell Mol Life Sci 53(2):141-151.
47. Liguri G, et al. (1986) A new acylphosphatase isoenzyme from human erythrocytes: purification, characterization, and primary structure. Biochemistry 25(24):8089-8094.
48. Ramponi G, Treves C, Guerritore A (1966) Continuous optical assay of acylphosphatase with benzoylphosphate as substrate. Experientia 22(11):705-706.