Chemical methods for peptide and protein production

Molecules

Volumn 18, Issue 4, 2013, Pages 4373-4388

  Chandrudu, Saranya ^a   Simerska, Pavla ^a   Toth, Istvan ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Native chemical ligation; Peptide; Peptide synthesis; Protein; Thioester

Indexed keywords

AMINO ACID; HYDROXYLAMINE; OXOACID; PEPTIDE;

CHEMISTRY; HUMAN; REVIEW; SYNTHESIS;

AMINO ACIDS; CHEMISTRY, PHARMACEUTICAL; HUMANS; HYDROXYLAMINE; KETO ACIDS; PEPTIDES;

EID: 84876768300     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18044373     Document Type: Review

References (102)

1. Lichtenthaler, F.W. Emil fischer, his personality, his achievements, and his scientific progeny. Eur. J. Org. Chem. 2002, 24, 4095-4122.
2. Fischer, E.; Fourneau, E. Ueber einige derivate des glykocolls. Ber. Dtsch. Chem. Ges. 1901, 34, 2868-2877.
3. Merrifield, R.B. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 1963, 85, 2149-2154.
4. Anderson, G.W.; McGregor, A.C. T-butyloxycarbonylamino acids and their use in peptide synthesis. J. Am. Chem. Soc. 1957, 79, 6180-6183.
5. Grapsas, I.; Cho, Y.J.; Mobashery, S. N-(tert-butoxycarbonyloxy)-5- norbornene-endo-2, 3- dicarboximide, a reagent for the regioselective introduction of the tert-butoxycarbonyl (boc) protective group at unhindered amines: Application to amino glycoside chemistry. J. Org. Chem. 1994, 59, 1918-1922.
6. Pedersen, S.L.; Tofteng, A.P.; Malik, L.; Jensen, K.J. Microwave heating in solid-phase peptide synthesis. Chem. Soc. Rev. 2012, 41, 1826-1844.
7. Schnölzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S.B.H. In situ neutralization in boc-chemistry solid phase peptide synthesis. Int. J. Pept. Prot. Res. 2009, 40, 180-193.
8. King, D.S.; Fields, C.G.; Fields, G.B. A cleavage method which minimizes side reactions following fmoc solid phase peptide synthesis. Int. J. Pept. Prot. Res. 2009, 36, 255-266.
9. Berman, A.L.; Kolker, E.; Trifonov, E.N. Underlying order in protein sequence organization. P. Natl. A. Sci. USA 1994, 91, 4044-4047.
10. Kemp, D.; Leung, S.L.; Kerkman, D.J. Models that demonstrate peptide bond formation by prior thiol capture i. Capture by disulfide formation. Tetrahedron Lett. 1981, 22, 181-184.
11. Skwarczynski, M.; Kiso, Y. Application of the on intramolecular acyl migration reaction in medicinal chemistry. Curr. Med. Chem. 2007, 14, 2813-2823.
12. Carpino, L.A. Oxidative reactions of hydrazines. Iv. Elimination of nitrogen from 1, 1-disubstituted-2-arenesulfonhydrazides1-4. J. Am. Chem. Soc. 1957, 79, 4427-4431.
13. Sakakibara, S.; Kishida, Y.; Nishizawa, R.; Shimonishi, Y. Use of anhydrous hydrogen fluoride in peptide synthesis. Procedures for the syntheses of simple peptides. Bull. Chem. Soc. Jpn. 1968, 41, 438.
14. Pietta, P.; Marshall, G.R. Amide protection and amide supports in solid-phase peptide synthesis. J. Chem. Soc. Chem. Comm. 1970, 11, 650-651.
15. Carpino, L.A.; Han, G.Y. 9-Fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group. J. Am. Chem. Soc. 1970, 92, 5748-5749.
16. Wang, S.-S. P-alkoxybenzyl alcohol resin and p- alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments. J. Am. Chem. Soc. 1973, 95, 1328-1333.
17. Barany, G.; Merrifield, R. A new amino protecting group removable by reduction. Chemistry of the dithiasuccinoyl (dts) function. J. Am. Chem. Soc. 1977, 99, 7363-7365.
18. Rink, H. Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenylmethylester resin. Tetrahedron Lett. 1987, 28, 3787-3790.
19. Sieber, P. A new acid-labile anchor group for the solid-phase synthesis of c-terminal peptide amides by the fmoc method. Tetrahedron Lett. 1987, 28, 2107-2110.
20. Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Rapid in situ neutralization protocols for boc and fmoc solid-phase chemistries. Methods Enzymol. 1997, 289, 14-29.
21. Dawson, P.E.; Muir, T.W.; Clark-Lewis, I.; Kent, S.B.H. Synthesis of proteins by native chemical ligation. Science 1994, 266, 776-778.
22. Liu, C.F.; Rao, C.; Tam, J.P. Orthogonal ligation of unprotected peptide segments through pseudoproline formation for the synthesis of hiv-1 protease analogs. J. Am. Chem. Soc. 1996, 118, 307-312.
23. Wöhr, T.; Wahl, F.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X.; Mutter, M. Pseudo-prolines as a solubilizing, structure-disrupting protection technique in peptide synthesis. J. Am. Chem. Soc. 1996, 118, 9218-9227.
24. Carpino, L.A.; Ghassemi, S.; Ionescu, D.; Ismail, M.; Sadat-Aalaee, D.; Truran, G.A.; Mansour, E.; Siwruk, G.A.; Eynon, J.S.; Morgan, B. Rapid, continuous solution-phase peptide synthesis: Application to peptides of pharmaceutical interest. Org. Process Res. Dev. 2003, 7, 28-37.
25. Nishiuchi, Y.; Inui, T.; Nishio, H.; Bódi, J.; Kimura, T.; Tsuji, F.I.; Sakakibara, S. Chemical synthesis of the precursor molecule of the aequorea green fluorescent protein, subsequent folding, and development of fluorescence. P. Natl. A. Sci. USA 1998, 95, 13549-13554.
26. Vigneaud, V.; Ressler, C.; Swan, C.J.M.; Roberts, C.W.; Katsoyannis, P.G.; Gordon, S. The synthesis of an octapeptide amide with the hormonal activity of oxytocin. J. Am. Chem. Soc. 1953, 75, 4879-4880.
27. du Vigneaud, V.; Ressler, C.; Swan, J.M.; Roberts, C.W.; Katsoyannis, P.G. The synthesis of oxytocin1. J. Am. Chem. Soc. 1954, 76, 3115-3121.
28. Carpino, L.A. The 9-fluorenylmethyloxycarbonyl family of base-sensitive amino-protecting groups. Accounts Chem. Res. 1987, 20, 401-407.
29. Chen, S.; Janda, K.D. Total synthesis of naturally occurring prostaglandin f2α on a non-crosslinked polystyrene support. Tetrahedron Lett. 1998, 39, 3943-3946.
30. Gutte, B.; Merrifield, R. The synthesis of ribonuclease a. J. Biol. Chem. 1971, 246, 1922-1941.
31. Palasek, S.A.; Cox, Z.J.; Collins, J.M. Limiting racemization and aspartimide formation in microwave-enhanced fmoc solid phase peptide synthesis. Pept. Sci. 2006, 13, 143-148.
32. Skwarczynski, M.; Hussein, W.M.; Liu, T.-Y.; Toth, I. Microwave-assisted synthesis of difficult sequence-containing peptide using the isopeptide method. Org. Biomol. Chem. 2013, 11, 2370-2376.
33. Kemp, D.; Kerkman, D.J. Models that demonstrate peptide bond formation by prior thiol capture - II capture by organomercury derivatives. Tetrahedron Lett. 1981, 22, 185-186.
34. Fotouhi, N.; Galakatos, N.G.; Kemp, D. Peptide synthesis by prior thiol capture. 6. Rates of the disulfide-bond-forming capture reaction and demonstration of the overall strategy by synthesis of the c-terminal 29-peptide sequence of bpti. J. Org. Chem. 1989, 54, 2803-2817.
35. Schnölzer, M.; Kent, S. Constructing proteins by dovetailing unprotected synthetic peptides: Backbone-engineered hiv protease. Science 1992, 256, 221.
36. Dirksen, A.; Meijer, E.; Adriaens, W.; Hackeng, T.M. Strategy for the synthesis of multivalent peptide-based nonsymmetric dendrimers by native chemical ligation. Chem. Commun. 2006, 15, 1667-1669.
37. Dawson, P.E.; Kent, S.B.H. Synthesis of native proteins by chemical ligation 1. Annu. Rev. Biochem. 2000, 69, 923-960.
38. Camarero, J.A.; Shekhtman, A.; Campbell, E.A.; Chlenov, M.; Gruber, T.M.; Bryant, D.A.; Darst, S.A.; Cowburn, D.; Muir, T.W. Autoregulation of a bacterial σ factor explored by using segmental isotopic labeling and nmr. P. Natl. A. Sci. USA 2002, 99, 8536-8541.
39. Cowburn, D.; Muir, T.W. Segmental isotopic labeling using expressed protein ligation. Methods Enzymol. 2001, 339, 41-54.
40. Ficht, S.; Dose, C.; Seitz, O. As fast and selective as enzymatic ligations: Unpaired nucleobases increase the selectivity of DNA-controlled native chemical pna ligation. ChemBioChem 2005, 6, 2098-2103.
41. Lovrinovic, M.; Niemeyer, C.M. Microtiter plate-based screening for the optimization of DNA- protein conjugate synthesis by means of expressed protein ligation. ChemBioChem 2006, 8, 61-67.
42. Paramonov, S.E.; Gauba, V.; Hartgerink, J.D. Synthesis of collagen-like peptide polymers by native chemical ligation. Macromolecules 2005, 38, 7555-7561.
43. Zhong, W.; Skwarczynski, M.; Fujita, Y.; Simerska, P.; Good, M.F.; Toth, I. Design and synthesis of lipopeptide-carbohydrate assembled multivalent vaccine candidates using native chemical ligation. Aust. J. Chem. 2009, 62, 993-999.
44. Blanco-Canosa, J.B.; Dawson, P.E. An efficient fmoc-spps approach for the generation of thioester peptide precursors for use in native chemical ligation. Angew. Chem. Int. Edit. 2008, 47, 6851-6855.
45. Bu, X.; Xie, G.; Law, C.W.; Guo, Z. An improved deblocking agent for direct fmoc solid-phase synthesis of peptide thioesters. Tetrahedron Lett. 2002, 43, 2419-2422.
46. Ollivier, N.; Behr, J.B.; El-Mahdi, O.; Blanpain, A.; Melnyk, O. Fmoc solid-phase synthesis of peptide thioesters using an intramolecular n, s-acyl shift. Org. Lett. 2005, 7, 2647-2650.
47. Alsina, J.; Yokum, T.S.; Albericio, F.; Barany, G. Backbone amide linker (bal) strategy for n α- 9-fluorenylmethoxycarbonyl (fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters1. J. Org. Chem. 1999, 64, 8761-8769.
48. Pentelute, B.L.; Gates, Z.P.; Tereshko, V.; Dashnau, J.L.; Vanderkooi, J.M.; Kossiakoff, A.A.; Kent, S.B.H. X-ray structure of snow flea antifreeze protein determined by racemic crystallization of synthetic protein enantiomers. J. Am. Chem. Soc. 2008, 130, 9695-9701.
49. Pentelute, B.L.; Gates, Z.P.; Dashnau, J.L.; Vanderkooi, J.M.; Kent, S.B.H. Mirror image forms of snow flea antifreeze protein prepared by total chemical synthesis have identical antifreeze activities. J. Am. Chem. Soc. 2008, 130, 9702-9707.
50. Brik, A.; Keinan, E.; Dawson, P.E. Protein synthesis by solid-phase chemical ligation using a safety catch linker. J. Org. Chem. 2000, 65, 3829-3835.
51. Bang, D.; Pentelute, B.L.; Kent, S.B. Kinetically controlled ligation for the convergent chemical synthesis of proteins. Angew. Chem. Int. Ed. 2006, 45, 3985-3988.
52. Leleu, S.; Penhoat, M.; Bouet, A.; Dupas, G.; Papamicaël, C.; Marsais, F.; Levacher, V. Amine capture strategy for peptide bond formation by means of quinolinium thioester salts. J. Am. Chem. Soc. 2005, 127, 15668-15669.
53. Perler, F.B.; Adam, E. Protein splicing and its applications. Curr. Opin. Biotech. 2000, 11, 377-383.
54. Muir, T.W.; Sondhi, D.; Cole, P.A. Expressed protein ligation: A general method for protein engineering. P. Natl. A. Sci. USA 1998, 95, 6705-6710.
55. Nilsson, B.L.; Hondal, R.J.; Soellner, M.B.; Raines, R.T. Protein assembly by orthogonal chemical ligation methods. J. Am. Chem. Soc. 2003, 125, 5268-5269.
56. Saleh, L.; Perler, F.B. Protein splicing in cis and in trans. Chem. Rec. 2006, 6, 183-193.
57. De Rosa, L.; Cortajarena, A.L.; Romanelli, A.; Regan, L.; D'Andrea, L.D. Site-specific protein double labeling by expressed protein ligation: Applications to repeat proteins. Org. Biomol. Chem. 2012, 10, 273-280.
58. Saxon, E.; Armstrong, J.I.; Bertozzi, C.R. A "traceless" staudinger ligation for the chemoselective synthesis of amide bonds. Org. Lett. 2000, 2, 2141-2143.
59. Soellner, M.B.; Nilsson, B.L.; Raines, R.T. Staudinger ligation of α-azido acids retains stereochemistry. J. Org. Chem. 2002, 67, 4993-4996.
60. Saxon, E.; Bertozzi, C.R. Cell surface engineering by a modified staudinger reaction. Science 2000, 287, 2007-2010.
61. Szymański, W.; Wu, B.; Poloni, C.; Janssen, D.B.; Feringa, B.L. Azobenzene photoswitches for staudinger-bertozzi ligation. Angew. Chem. Int. Ed. 2013, 52, 2068-2072.
62. Li, P.; Wang, L. One-pot synthesis of 1, 2, 3-triazoles from benzyl and alkyl halides, sodium azide and alkynes in water under transition-metal-catalyst free reaction conditions. Lett. Org. Chem. 2007, 4, 23-26.
63. Manetsch, R.; Krasinski, A.; Radic, Z.; Raushel, J.; Taylor, P.; Sharpless, K.B.; Kolb, H.C. In situ click chemistry: Enzyme inhibitors made to their own specifications. J. Am. Chem. Soc. 2004, 126, 12809-12818.
64. Meutermans, W.D.F.; Golding, S.W.; Bourne, G.T.; Miranda, L.P.; Dooley, M.J.; Alewood, P.F.; Smythe, M.L. Synthesis of difficult cyclic peptides by inclusion of a novel photolabile auxiliary in a ring contraction strategy. J. Am. Chem. Soc. 1999, 121, 9790-9796.
65. Sohma, Y.; Taniguchi, A.; Yoshiya, T.; Chiyomori, Y.; Fukao, F.; Nakamura, S.; Skwarczynski, M.; Okada, T.; Ikeda, K.; Hayashi, Y. 'Click peptide': A novel 'o-acyl isopeptide method'for peptide synthesis and chemical biology-oriented synthesis of amyloid β peptide analogues. J. Pept. Sci. 2006, 12, 823-828.
66. Sohma, Y.; Sasaki, M.; Hayashi, Y.; Kimura, T.; Kiso, Y. Novel and efficient synthesis of difficult sequence-containing peptides through o-n intramolecular acyl migration reaction of o-acyl isopeptides. Chem. Commun. 2004, 124-125. DOI:10.1039/b312129a
67. Fang, G.M.; Li, Y.M.; Shen, F.; Huang, Y.C.; Li, J.B.; Lin, Y.; Cui, H.K.; Liu, L. Protein chemical synthesis by ligation of peptide hydrazides. Angew. Chem. Int. Ed. 2011, 50, 7645-7649.
68. Fang, G.M.; Wang, J.X.; Liu, L. Convergent chemical synthesis of proteins by ligation of peptide hydrazides. Angew. Chem. Int. Ed. 2012, 51, 10347-10350.
69. Pattabiraman, V.R.; Ogunkoya, A.O.; Bode, J.W. Chemical protein synthesis by chemoselective α-ketoacid-hydroxylamine (kaha) ligations with 5-oxaproline. Angew. Chem. Int. Ed. 2012, 51, 5114-5118.
70. Ogunkoya, A.O.; Pattabiraman, V.R.; Bode, J.W. Sequential α-ketoacid-hydroxylamine (kaha) ligations: Synthesis of c-terminal variants of the modifier protein ufm1. Angew. Chem. Int. Ed. 2012, 51, 9693-9697.
71. Bode, J.W.; Fox, R.M.; Baucom, K.D. Chemoselective amide ligations by decarboxylative condensations of n-alkylhydroxylamines and α-ketoacids. Angew. Chem. Int. Ed. 2006, 45, 1248-1252.
72. Carrillo, N.; Davalos, E.A.; Russak, J.A.; Bode, J.W. Iterative, aqueous synthesis of β3-oligopeptides without coupling reagents. J. Am. Chem. Soc. 2006, 128, 1452-1453.
73. Hughes, B. 2009 fda drug approvals. Nat. Rev. Drug. Discov. 2010, 9, 89-92.
74. Mullard, A. 2010 fda drug approvals. Nat. Rev. Drug. Discov. 2011, 10, 82-85.
75. Mullard, A. 2011 fda drug approvals. Nat. Rev. Drug. Discov. 2012, 11, 91-94.
76. Mullard, A. 2012 fda drug approvals. Nat. Rev. Drug. Discov. 2013, 12, 87-90.
77. Vlieghe, P.; Lisowski, V.; Martinez, J.; Khrestchatisky, M. Synthetic therapeutic peptides: Science and market. Drug Discov. Today 2010, 15, 40-56.
78. Ayoub, M.; Scheidegger, D. Peptide drugs, overcoming the challenges, a growing business. Chim. Oggi. 2006, 24, 46-48.
79. Takahashi, H.; Okamoto, M.; Shimodaira, S.; Tsujitani, S.-I.; Nagaya, M.; Ishidao, T.; Kishimoto, J.; Yonemitsu, Y. Impact of dendritic cell vaccines pulsed with wilms' tumour-1 peptide antigen on the survival of patients with advanced non-small cell lung cancers. Eur. J. Cancer 2012, 49, 852-859.
80. Sosinowski, T.; Eisenbarth, G.S. Type 1 diabetes: Primary antigen/peptide/register/trimolecular complex. Immunol. Res. 2012, 55, 270-276.
81. Chen, H.H.; Glockner, J.F.; Schirger, J.A.; Cataliotti, A.; Redfield, M.M.; Burnett, J.C. Novel protein therapeutics for systolic heart failure: chronic subcutaneous B-type natruiuretic peptide. J. Am. Coll. Cardiol. 2012, 60, 2305-2312.
82. Dawgul, M.; Baranska-Rybak, W.; Kamysz, E.; Karafova, A.; Nowicki, R.; Kamysz, W. Activity of short lipopeptides and conventional antimicrobials against planktonic cells and biofilms formed by clinical strains of staphylococcus aureus. Future 2012, 4, 1541-1551.
83. Coles, D.J.; Simerska, P.; Fujita, Y.; Toth, I. The influence of incorporating lipids or liposaccharides on the particle size of peptide therapeutics. Biopolymers Pept. Sci. 2011, 96, 172-176.
84. Gibbons, W.A.; Hughes, R.A.; Charalambous, M.; Christodoulou, M.; Szeto, A.; Aulabaugh, A.E.; Mascagni, P.; Toth, I. Lipidic peptides, i. Synthesis, resolution and structural elucidation of lipidic amino acids and their homo-and hetero-oligomers. Liebigs. Ann. Chem. 2006, 1990, 1175-1183.
85. Kellam, B.; Drouillat, B.; Dekany, G.; Starr, M.S.; Toth, I. Synthesis and in vitro evaluation of lipoamino acid and carbohydrate-modified enkephalins as potential antinociceptive agents. Int. J. Pharm. 1998, 161, 55-64.
86. Ross, B.P.; Falconer, R.A.; Toth, I. N-1-(4, 4-dimethyl-2, 6-dioxocyclohex-1-ylidene) ethyl (n-dde) lipoamino acids. Molbank 2008, 2008, M566.
87. Goodwin, D.; Simerska, P.; Toth, I. Peptides as therapeutics with enhanced bioactivity. Curr. Med. Chem. 2012, 19, 4451-4461.
88. Simerska, P.; Moyle, P.M.; Toth, I. Modern lipid-, carbohydrate-, and peptide-based delivery systems for peptide, vaccine, and gene products. Med. Res. Rev. 2009, 31, 520-547.
89. Varamini, P.; Mansfeld, F.M.; Blanchfield, J.T.; Wyse, B.D.; Smith, M.T.; Toth, I. Lipoendomorphin- 1 derivatives with systemic activity against neuropathic pain without producing constipation. PLOS One 2012, 7, e41909.
90. Simerska, P.; Abdel-Aal, A.-B.M.; Fujita, Y.; Moyle, P.M.; McGeary, R.P.; Batzloff, M.R.; Olive, C.; Good, M.F.; Toth, I. Development of a liposaccharide-based delivery system and its application to the design of group a streptococcal vaccines. J. Med. Chem. 2008, 51, 1447-1452.
91. Simerska, P.; Abdel-Aal, A.B.M.; Fujita, Y.; Batzloff, M.R.; Good, M.F.; Toth, I. Synthesis and in vivo studies of carbohydrate-based vaccines against group a streptococcus. Biopolymers Pept. Sci. 2008, 90, 611-616.
92. Zhong, W.; Skwarczynski, M.; Simerska, P.; Good, M.F.; Toth, I. Development of highly pure α- helical lipoglycopeptides as self-adjuvanting vaccines. Tetrahedron 2009, 65, 3459-3464.
93. Abdel-Aal, A.-B.M.; Batzloff, M.R.; Fujita, Y.; Barozzi, N.; Faria, A.; Simerska, P.; Moyle, P.M.; Good, M.F.; Toth, I. Structure-activity relationship of a series of synthetic lipopeptide selfadjuvanting group a streptococcal vaccine candidates. J. Med. Chem. 2007, 51, 167-172.
94. Zaman, M.; Abdel-Aal, A.-B.M.; Fujita, Y.; Ziora, Z.M.; Batzloff, M.R.; Good, M.F.; Toth, I. Structure-activity relationship for the development of a self-adjuvanting mucosally active lipopeptide vaccine against streptococcus pyogenes. J. Med. Chem. 2012, 55, 8515-8523.
95. Skwarczynski, M.; Dougall, A.M.; Khoshnejad, M.; Chandrudu, S.; Pearson, M.S.; Loukas, A.; Toth, I. Peptide-based subunit vaccine against hookworm infection. Plos One 2012, 7, e46870.
96. Montague, C.T.; Farooqi, I.S.; Whitehead, J.P.; Soos, M.A.; Rau, H.; Wareham, N.J.; Sewter, C.P.; Digby, J.E.; Mohammed, S.N.; Hurst, J.A. Congenital leptin deficiency is associated with severe early-onset obesity in humans. Nature 1997, 387, 903-908.
97. Shi, L.; Sings, H.; Bryan, J.; Wang, B.; Wang, Y.; Mach, H.; Kosinski, M.; Washabaugh, M.; Sitrin, R.; Barr, E. Gardasil®: Prophylactic human papillomavirus vaccine development-from bench top to bed-side. Clin. Pharmacol. Ther. 2007, 81, 259-264.
98. Schafmeister, C.E.; Po, J.; Verdine, G.L. An all-hydrocarbon cross-linking system for enhancing the helicity and metabolic stability of peptides. J. Am. Chem. Soc. 2000, 122, 5891-5892.
99. Verdine, G.L.; Hilinski, G. Stapled peptides for intracellular drug targets. Methods Enzymol. 2012, 503, 3-33.
100. Walensky, L.D.; Kung, A.L.; Escher, I.; Malia, T.J.; Barbuto, S.; Wright, R.D.; Wagner, G.; Verdine, G.L.; Korsmeyer, S.J. Activation of apoptosis in vivo by a hydrocarbon-stapled BH3 helix. Sci. Signal. 2004, 305, 1466-1470.
101. Rojas-Cervellera, V.c.; Giralt, E.; Rovira, C. Staple motifs, initial steps in the formation of thiolate-protected gold nanoparticles: How do they form? Inorg. Chem. 2012, 51, 11422-11429.
102. Green, B.R.; Klein, B.D.; Lee, H.-K.; Smith, M.D.; Steve White, H.; Bulaj, G. Cyclic analogs of galanin and neuropeptide Y by hydrocarbon stapling. Bioorg. Med. Chem. 2012, 21, 303-310.