Application of the logic of cysteine-free native chemical ligation to the synthesis of Human Parathyroid Hormone (hPTH)

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

Volumn 108, Issue 15, 2011, Pages 5986-5989

  Shang, Shiying ^a   Tan, Zhongping ^a   Danishefsky, Samuel J ^b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Alanine ligation; Desulfurization; Leucine ligation; Peptide; Valine ligation

Indexed keywords

PARATHYROID HORMONE; POLYPEPTIDE; THIOL DERIVATIVE;

CHEMICAL MODIFICATION; CONFERENCE PAPER; CYSTEINE FREE NATIVE CHEMICAL LIGATION; DESULFURIZATION; HORMONE SYNTHESIS; HUMAN; PRIORITY JOURNAL;

EID: 79955027300     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1103118108     Document Type: Article

References (41)

1. Reid RE (2000) Peptide and protein drug analysis (M. Dekker, New York), pp 1-885.
2. Dawson PE, Muir TW, Clark-Lewis I, Kent SB (1994) Synthesis of proteins by native chemical ligation. Science 266:776-779. (Pubitemid 24359280)
3. Tam JP, Lu YA, Liu CF, Shao J (1995) Peptide synthesis using unprotected peptides through orthogonal coupling methods. Proc Natl Acad Sci USA 92:12485-12489. (Pubitemid 26014094)
4. Tam JP, Yu QT (1998) Methionine ligation strategy in the biomimetic synthesis of parathyroid hormones. Biopolymers 46:319-327.
5. Yan LZ, Dawson PE (2001) Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization. J Am Chem Soc 123:526-533. (Pubitemid 32105995)
6. Botti P, Tchertchian S (2006) Side-chain extended ligation Patent No. WO2006133962.
7. Crich D, Banerjee A (2007) Native chemical ligation at phenylalanine. J Am Chem Soc 129:10064-10065. (Pubitemid 47312928)
8. Pentelute BL, Kent SB (2007) Selective desulfurization of cysteine in the presence of Cys(Acm) in polypeptides obtained by native chemical ligation. Org Lett 9:687-690.
9. Wan Q, Danishefsky SJ (2007) Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides. Angewandte Chemie International Edition 46:9248-9252. (Pubitemid 350292152)
10. Haase C, Rohde H, Seitz O (2008) Native chemical ligation at valine. Angewandte Chemie International Edition 47:6807-6810.
11. Chen J, Wan Q, Yuan Y, Zhu J, Danishefsky SJ (2008) Native chemical ligation at valine: a contribution to peptide and glycopeptide synthesis. Angewandte Chemie International Edition 47:8521-8524.
12. Yang R, Pasunooti KK, Li F, Liu XW, Liu CF (2009) Dual native chemical ligation at lysine. J Am Chem Soc 131:13592-13593.
13. Kumar KSA, Haj-Yahya M, Olschewski D, Lashuel HA, Brik A (2009) Highly efficient and chemoselective peptide ubiquitylation. Angewandte Chemie International Edition 48:8090-8094.
14. Chen J, Wang P, Zhu JL, Wan Q, Danishefsky SJ (2010) A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides. Tetrahedron 66:2277-2283.
15. Harpaz Z, Siman P, Kumar KS, Brik A (2010) Protein synthesis assisted by native chemical ligation at leucine. Chembiochem 11:1232-1235.
16. Metanis N, Keinan E, Dawson PE (2010) Traceless ligation of cysteine peptides using selective deselenization. Angewandte Chemie International Edition 49:7049-7053.
17. Tan Z, Shang S, Danishefsky SJ (2010) Insights into the finer issues of native chemical ligation: an approach to cascade ligations. Angewandte Chemie International Edition 49:9500-9503.
18. Potts JT (2005) Parathyroid hormone: past and present. J Endocrinol 187:311-325. (Pubitemid 43020252)
19. Potts JT, Gardella TJ (2007) Progress, paradox, and potential: parathyroid hormone research over five decades. Ann NY Acad Sci 1117:196-208. (Pubitemid 350191296)
20. Talmage RV, Mobley HT (2008) Calcium homeostasis: reassessment of the actions of parathyroid hormone. Gen Comp Endocrinol 156:1-8.
21. Dominguez LJ, Scalisi R, BarbagalloM(2010) Therapeutic options in osteoporosis. Acta Biomedica 81:55-65.
22. EllegaardM, Jorgensen NR, Schwarz P (2010) Parathyroid hormone and bone healing. Calcif Tissue Int 87:1-13.
23. Fraser WD (2009) Hyperparathyroidism. Lancet 374:145-158.
24. Bieglmayer C, Prager G, Niederle B (2002) Kinetic analyses of parathyroid hormone clearance as measured by three rapid immunoassays during parathyroidectomy. Clin Chem 48:1731-1738.
25. Abraham AK, et al. (2009) Mechanism-based pharmacokinetic/pharmacodynamic model of parathyroid hormone-calcium homeostasis in rats and humans. J Pharmacol Exp Ther 330:169-178.
26. Potts JT, Jr, Gardella TJ, Juppner H, Kronenberg HM (1997) Structure based design of parathyroid hormone analogs. J Endocrinol 154:S15-21.
27. Willick GE, Morley P, Whitfield JF (2004) Constrained analogs of osteogenic peptides. Curr Med Chem 11:2867-2881. (Pubitemid 39377887)
28. Voloshchuk N, Montclare JK (2010) Incorporation of unnatural amino acids for synthetic biology. Mol Biosyst 6:65-80.
29. Reissmann S, Imhof D (2004) Development of conformationally restricted analogues of bradykinin and somatostatin using constrained amino acids and different types of cyclization. Curr Med Chem 11:2823-2844. (Pubitemid 39377885)
30. Kimura T, Takai M, Masui Y, Morikawa T, Sakakibara S (1981) Strategy for the synthesis of large peptides-an application to the total synthesis of Human Parathyroid- Hormone [hPTH(1-84)]. Biopolymers 20:1823-1832. (Pubitemid 12243422)
31. Fairwell T, et al. (1983) Total solid-phase synthesis, purification, and characterization of Human Parathyroid Hormone-(1-84). Biochemistry 22:2691-2697. (Pubitemid 13103328)
32. Goud NA, et al. (1991) Solid-phase synthesis and biologic activity of Human Parathyroid Hormone (1-84). J Bone Miner Res 6:781-789.
33. Fuentes G, Page K, Chantell CA, Patel H, Menakuru M (2009) Fast conventional synthesis of Human Parathyroid Hormone 1-84. Chim Oggi 27:31-33.
34. Merrifield RB (1963) Solid phase peptide synthesis. I. synthesis of a tetrapeptide. J Am Chem Soc 85:2149-2154.
35. Lloydwilliams P, Albericio F, Giralt E (1993) Convergent solid-phase peptide-synthesis. Tetrahedron 49:11065-11133.
36. Sakakibara S (1995) Synthesis of large peptides in solution. Biopolymers 37:17-28.
37. Bang D, Pentelute BL, Kent SB (2006) Kinetically controlled ligation for the convergent chemical synthesis of proteins. Angewandte Chemie International Edition 45:3985-3988. (Pubitemid 44105704)
38. Johnson EC, Kent SB (2006) Insights into the mechanism and catalysis of the native chemical ligation reaction. J Am Chem Soc 128:6640-6646.
39. Zull JE, Smith SK, Wiltshire R (1990) Effect of methionine oxidation and deletion of amino-terminal residues on the conformation of parathyroid hormone: circular dichroism studies. J Biol Chem 265:5671-5676.
40. Alexander P, Orban J, Bryan P (1992) Kinetic analysis of folding and unfolding the 56 amino acid IgG-binding domain of streptococcal protein G. Biochemistry 31:7243-7248.
41. Engfeldt T, Renberg B, Brumer H, Nygren PA, Karlstrom AE (2005) Chemical synthesis of triple-labeled three-helix bundle binding proteins for specific fluorescent detection of unlabelled protein. Chembiochem 6:1043-1050. (Pubitemid 40825345)