Chemical synthesis of proteins using hydrazide intermediates

National Science Review

Volumn 3, Issue 1, 2016, Pages 107-116

  Huang, Yi Chao ^a   Fang, Ge Min ^a   Liu, Lei ^a  

^a Tsinghua University   (China)

Author keywords

Native chemical ligationcover date; Peptide hydrazide; Protein chemical synthesis; Protein chemistry; Protein hydrazide

Indexed keywords

EID: 84963829840     PISSN: 20955138     EISSN: 2053714X     Source Type: Journal    
DOI: 10.1093/nsr/nwv072     Document Type: Review

References (69)

1. Hackenberger, CPR and Schwarzer, D. Chemoselective ligation and modification strategies for peptides and proteins. Angew Chem Int Ed 2008; 47: 10030-74
2. Walsh, CT, Garneau-Tsodikova, S and Gatto, GJ, Jr. Protein posttranslational modifications: the chemistry of proteome diversifications. Angew Chem Int Ed 2005; 44: 7342-72
3. Flavell, RR and Muir, TW. Expressed protein ligation (EPL) in the study of signal transduction, ion conduction, and chromatin biology. Acc Chem Res 2009; 42: 107-16
4. Sletten, EM and Bertozzi, CR. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed 2009; 48: 6974-98
5. Lindegren, CR and Niemann, C. The apparent ionization constants of acethydrazide and glycylhydrazide. J Am Chem Soc 1949; 71: 1504
6. Park, KD, Liu, R and Kohn, H. Useful tools for biomolecule isolation, detection, and identification: acylhydrazone-based cleavable linkers. Chem Biol 2009; 16: 763-72
7. Zhang, H, Li, X-J and Martin, DB et al. Identification and quantification of N-linked glycoproteins using hydrazide chemistry, stable isotope labeling and mass spectrometry. Nat Biotech 2003; 21: 660-6
8. Carrico, IS, Carlson, BL and Bertozzi, CR. Introducing genetically encoded aldehydes into proteins. Nat Chem Biol 2007; 3: 321-2
9. Gaertner, HF, Rose, K and Cotton, R et al. Construction of protein analogues by site-specific condensation of unprotected fragments. Bioconjug Chem 1992; 3: 262-8
10. Gaertner, HF, Offord, RE and Cotton, R et al. Chemo-enzymatic backbone engineering of proteins. J Biol Chem 1994; 269: 7224-30
11. Thom, J, Anderson, D and McGregor, J et al. Recombinant protein hydrazides: application to site-specific protein PEGylation. Bioconjug Chem 2011; 22: 1017-20
12. Avrutina, O, Schmoldt, H-U and Gabrijelcic-Geiger, D et al. Head-to-tail cyclized cysteine-knot peptides by a combined recombinant and chemical route of synthesis. ChemBioChem 2008; 9: 33-7
13. Dirksen, A, Dirksen, S and Hackeng, TM et al. Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry. J AmChem Soc 2006; 128: 15602-3
14. Xu, Y, Xu, L and Xia, Y et al. Fast and catalyst-free hydrazone ligation via ortho-halo-substituted benzaldehydes for protein C-terminal labeling at neutral pH. Chem Commun 2015; 51: 13189-92
15. Curtius, T. Verkettung von amidosauren I. Abhandlung. J Prakt Chem 1904; 70: 57-72
16. Yanaihara, N, Yanaihara, C and Dupuis, G et al. Studies on polypeptides. XLII. Synthesis and characterization of seven fragments spanning the entire sequence of ribonuclease T1. J Am Chem Soc 1969; 91: 2184-5
17. Felix, AM and Merrifield, RB. Azide solid phase peptide synthesis. J Am Chem Soc 1970; 92: 1385-91
18. El-Faham, A and Albericio, F. Peptide coupling reagents, more than a letter soup. Chem Rev 2011; 111: 6557-602
19. Wang, P, Layfield, R and Landon, M et al. Transfer active ester condensation: a novel technique for peptide segment coupling. Tetrahedron Lett 1998; 39: 8711-4
20. Wang, P, Shaw, KT and Whigham, B et al. Synthesis of peptide C-terminal derivatives using the transfer active ester condensation technique. Tetrahedron Lett 1998; 39: 8719-20
21. Wilkinson, KD, Smith, SE and O'Connor, L et al. A specific inhibitor of the ubiquitin activating enzyme: synthesis and characterization of adenosyl-phospho-ubiquitinol, a nonhydrolyzable ubiquitin adenylate analogue. Biochemistry 1990; 29: 7373-80
22. Borodovsky, A, Kessler, BM and Casagrande, R et al. A novel active site-directed probe specific for deubiquitylating enzymes reveals proteasome association of USP14. EMBO J 2001; 20: 5187-96
23. Dawson, PE, Muir, TW and Clark-Lewis, I et al. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-9
24. Kent, SBH. Total chemical synthesis of proteins. Chem Soc Rev 2009; 38: 338-51
25. Chalker, JM, Bernardes, GJL and Lin, YA et al. Chemical modificiation of proteins at cysteine: opportunities in chemistry and biology. Chem Asian J 2009; 4: 630-40
26. Zheng, JS, Tang, S and Huang, YC et al. Development of new thioester equivalents for protein chemical synthesis. Acc Chem Res 2013; 46: 2475-84
27. Camarero, JA, Hackel, BJ and de Yoreo, JJ et al. Fmoc-based synthesis of peptide a-thioesters using an aryl hydrazine support. J Org Chem 2004; 69: 4145-51
28. Fang, GM, Li, YM and Shen, F et al. Protein chemical synthesis by ligation of peptide hydrazides. Angew Chem Int Ed 2011; 50: 7645-9
29. Zheng, JS, Tang, S and Qi, YK et al. Chemical synthesis of proteins using peptide hydrazides as thioester surrogates. Nat Protoc 2013; 8: 2483-95
30. Raibaut, L, Ollivier, N and Melnyk, O. Sequential native peptide ligation strategies for total chemical protein synthesis. Chem Soc Rev 2012; 41: 7001-15
31. Bang, D and Kent, SBH. A one-pot total synthesis of crambin. Angew Chem Int Ed 2004; 43: 2534-8
32. Mende, F and Seitz, O. 9-Fluorenylmethoxycarbonyl-based solidphase synthesis of peptide a-thioesters. Angew Chem Int Ed 2011; 50: 1232-40
33. Fang, GM, Wang, JX and Liu, L. Convergent chemical synthesis of proteins by ligation of peptide hydrazides. Angew Chem Int Ed 2012; 51: 10347-50
34. Hojo, H, Onuma, Y and Akimoto, Y et al. N-alkyl cysteineassisted thioesterification of peptides. Tetrahedron Lett 2007; 48: 25-8
35. Kawakami, T and Aimoto, S. Sequential peptide ligation by using a controlled cysteinyl prolyl ester (CPE) autoactivating unit. Tetrahedron Lett 2007; 48: 1903-5
36. Ollivier, N, Dheur, J and Mhidia, R et al. Bis(2-sulfanylethyl)amino native peptide ligation. Org Lett 2010; 12: 5238-41
37. Sato, K, Shigenaga, A and Tsuji, K et al. N-sulfanylethylanilide peptide as a crypto-thioester peptide. ChemBioChem 2011; 12: 1840-4
38. Hou, W, Zhang, XH and Li, FP et al. Peptidyl N,N-bis(2-mercaptoethyl)-amides as thioester precursors for native chemical ligation. Org Lett 2011; 13: 386-9
39. Taichi,M, Hemu, X and Qiu, Y et al. A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift. Org Lett 2013; 15: 2620-3
40. Wang, JX, Fang, GM and He, Y et al. Peptide o-aminoanilides as cryptothioesters for protein chemical synthesis. Angew Chem Int Ed 2015; 54: 2194-8
41. Far, S and Melnyk, O. Synthesis of glyoxylyl peptides using a phosphine labile a,a'-diaminoacetic derivative. Tetrahedron Lett 2004; 45: 7163-5
42. Ollivier, N, Vicogne, J and Vallin, A et al. A one-pot three-segment ligation strategy for protein chemical synthesis. Angew Chem Int Ed 2012; 51: 209-13
43. Siman, P, Karthikeyan, SV and Nikolov, M et al. Convergent chemical synthesis of histone H2B protein for the site-specific ubiquitination at Lys34. Angew Chem Int Ed 2013; 52: 8059-63
44. Nepomniaschiy, N, Grimminger, V and Cohen, A et al. Switch peptide via staudinger reaction. Org Lett 2008; 10: 5243-6
45. Pan, M, He, Y and Wen, M et al. One-pot hydrazide-based native chemical ligation for efficient chemical synthesis and structure determination of toxin Mambalgin-1. Chem Commun 2014; 50: 5837-9
46. Li, JB, Li, YY and He, QQ et al. One-pot native chemical ligation of peptide hydrazides enables total synthesis of modified histones. Org Biomol Chem 2014; 12: 5435-41
47. Kemp, DS and Roberts, DC. New protective groups for peptide synthesis-II the Dobz group boron-derived affinity protection with the pdihydroxyborylbenzyloxycarbonylamino function. Tetrahedron Lett 1975; 16: 4629-32
48. Tang, S, Si, YY and Wang, ZP et al. An efficient one-pot four-segment condensation method for protein chemical synthesis. Angew Chem Int Ed 2015; 54: 5713-7
49. Casadio, F, Lu, X and Pollock, SB et al. H3R42me2a is a histone modification with positive transcriptional effects. Proc Natl Acad Sci USA 2013; 110: 14894-9
50. Reif, A, Siebenhaar, S and Troster, A et al. Semisynthesis of biologically active glycoforms of the human cytokine interleukin-6. Angew Chem Int Ed 2014; 53: 12125-31
51. Weinstock, MT, Jacobsen, MT and Kay, MS. Synthesis and folding of a mirrorimage enzyme reveals ambidextrous chaperone activity. Proc Natl Acad Sci USA 2014; 111: 11679-84
52. Zheng, J-S, Yu, M and Qi, Y-K et al. Expedient total synthesis of small to medium-sized membrane proteins via Fmoc chemistry. J Am Chem Soc 2014; 136: 3695-704
53. Chen, X, Tang, S and Zheng, J-S et al. Chemical synthesis of a two-photonactivatable chemokine and photon-guided lymphocyte migration in vivo. Nat Commun 2015; 6: 7220
54. Chang, H-N, Liu, B-Y and Qi, Y-K et al. Blocking of the PD-1/PD-L1 interaction by a D-peptide antagonist for cancer immunotherapy. Angew Chem Int Ed 2015; 54: 11760-4
55. Schumacher, TNM, Mayr, LM and Minor, DL, Jr et al. Identification of D-peptide ligands through mirror-image phage display. Science 1996; 271: 1854-7
56. Stavropoulos, G, Gatos, D and Magafa, V et al. Preparation of polymer-bound trityl-hydrazines and their applications in the solid phase synthesis of partially protected peptide hydrazides. Lett Pept Sci 1996; 2: 315-8
57. Zheng, J-S, Tang, S and Guo, Y et al. Synthesis of cyclic peptides and cyclic proteins via ligation of peptide hydrazides. ChemBioChem 2012; 13: 542-6
58. Huang, Y-C, Chen, C-C and Li, S-J et al. Facile synthesis of C-terminal peptide hydrazide and thioester NY-ESO-1 (A39-A68) from an Fmoc-hydrazine 2-chlorotrityl chloride resin. Tetrahedron 2014; 70: 2951-5
59. Qvortrup, K, Komnatnyy, VV and Nielsen, TE. A photolabile linker for the solidphase synthesis of peptide hydrazides and heterocycles. Org Lett 2014; 16: 4782-5
60. Bello, C, Kikul, F and Becker, CFW. Efficient generation of peptide hydrazides via direct hydrazinolysis of peptidyl-Wang-TentaGel resins. J Pept Sci 2015; 21: 201-7
61. Adams, AL, Cowper, B and Morgan, RE et al. Cysteine promoted C-terminal hydrazinolysis of native peptides and proteins. Angew Chem Int Ed 2013; 52: 13062-6
62. Tsuda, Y, Shigenaga, A and Tsuji, K et al. Development of a chemical methodology for the preparation of peptide thioesters applicable to naturally occuring peptides using a sequential quadruple acyl transfer system. ChemistryOpen 2015; 4: 448-52
63. Krezel, A, Kopera, E and Protas, AM et al. Sequence-specific Ni(II)-dependent peptide bond hydrolysis for protein engineering. Combinatorial library determination of optimal sequences. J Am Chem Soc 2010; 132: 3355-66
64. Li, Y-M, Yang, M-Y and Huang, Y-C et al. Ligation of expressed protein a-hydrazides via genetic incorporation of an a-hydroxy acid. ACS Chem Biol 2012; 7: 1015-22
65. Wilkinson, KD, Cox,MJ and Mayer, AN et al. Synthesis and characterization of ubiquitin ethyl ester, a new substrate for ubiquitin carboxy-terminal hydrolase. Biochemistry 1986; 25: 6644-9
66. Jones, RML and Offord, RE. The proteinase-catalysed synthesis of peptide hydrazides. Biochem J 1982; 203: 125-9
67. Li, Y-M, Li, Y-T and Pan, M et al. Irreversible site-specific hydrazinolysis of proteins by use of sortase. Angew Chem Int Ed 2014; 53: 2198-202
68. Liu, H and Li, X. Synthesis of highly-strained cyclic tetrapeptides via peptide hydrazide based ligation. Acta Chim Sinica 2014; 72: 1197-8
69. Huang, Y and Liu, L. Chemical synthesis of crystalline proteins. Sci China Chem 2015; 58: 1779-81