Tidbits for the synthesis of bis(2-sulfanylethyl)amido (SEA) polystyrene resin, SEA peptides and peptide thioesters

Journal of Peptide Science

Volumn 20, Issue 2, 2014, Pages 92-97

  Ollivier, Nathalie ^a   Raibaut, Laurent ^a   Blanpain, Annick ^a   Desmet, Rémi ^a   Dheur, Julien ^a   Mhidia, Reda ^a   Boll, Emmanuelle ^a   Drobecq, Hervé ^a   Pira, Silvain L ^a   Melnyk, Oleg ^a  

^a UNIV LILLE   (France)

Author keywords

bis(2 sulfanylethyl)amido (SEA); Fmoc SPPS; thioester; thiol exchange

Indexed keywords

3 MERCAPTOPROPIONIC ACID; BIS (2 SULFANYLETHYL) AMIDO POLYSTYRENE RESIN; PEPTIDE; RESIN; THIOESTER; UNCLASSIFIED DRUG; ESTER; POLYSTYRENE DERIVATIVE; SULFONAMIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; ATOM; CARBOXY TERMINAL SEQUENCE; OXIDATION; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; CHEMISTRY; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; ESTERS; PEPTIDES; POLYSTYRENES; RESINS, SYNTHETIC; SULFONAMIDES;

EID: 84892731343     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2580     Document Type: Article

References (47)

1. Raibaut L, Ollivier N, Melnyk O,. Sequential native peptide ligation strategies for total chemical protein synthesis. Chem. Soc. Rev. 2012; 41: 7001-7015.
2. Dawson PE, Muir TW, Clark-Lewis I, Kent SB,. Synthesis of proteins by native chemical ligation. Science 1994; 266: 776-779.
3. Kent SB,. Total chemical synthesis of proteins. Chem. Soc. Rev. 2009; 38: 338-351.
4. Canne LE, Botti P, Simon RJ, Chen Y, Dennis EA, Kent SBH,. Chemical protein synthesis by solid phase ligation of unprotected peptide segments. J. Am. Chem. Soc. 1999; 121: 8720-8727.
5. Cotton GJ, Muir TW,. Generation of a dual-labeled fluorescence biosensor for Crk-II phosphorylation using solid-phase expressed protein ligation. Chem. Biol. 2000; 7: 253-261.
6. Johnson EC, Durek T, Kent SB,. Total chemical synthesis, folding, and assay of a small protein on a water-compatible solid support. Angew. Chem. Int. Ed. 2006; 45: 3283-3287.
7. Raibaut L, Adihou H, Desmet R, Delmas AF, Aucagne V, Melnyk O,. Highly efficient solid phase synthesis of large polypeptides by iterative ligations of bis(2-sulfanylethyl)amido (SEA) peptide segments. Chem. Sci. 2013; 4: 4061-4066.
8. Hackenberger CP, Schwarzer D,. Chemoselective ligation and modification strategies for peptides and proteins. Angew. Chem. Int. Ed. 2008; 47: 10030-10074.
9. Mende F, Seitz O,. 9-Fluorenylmethoxycarbonyl-based solid-phase synthesis of peptide α-thioesters. Angew. Chem. Int. Ed. 2011; 50: 1232-1240.
10. 2. Bull. Soc. Chem. Jpn 1991; 64: 111-117.
11. Fields GB, Noble RL,. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. Int. J. Pept. Protein Res. 1990; 35: 161-214.
12. Clippingdale AB, Barrow CJ, Wade JD,. Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation. J. Pept. Sci. 2000; 6: 225-234.
13. Li X, Kawakami T, Aimoto S,. Direct preparation of peptide thioesters using an Fmoc solid-phase method. Tetrahedron Lett. 1998; 39: 8669-8672.
14. Raz R, Rademann J,. Fmoc-based synthesis of peptide thioesters for native chemical ligation employing a tert-butyl thiol linker. Org. Lett. 2011; 13: 1606-1609.
15. α-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters. J. Org. Chem. 1999; 64: 8761-8769.
16. Brask J, Albericio F, Jensen KJ,. Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters. Org. Lett. 2003; 5: 2951-2953.
17. Tulla-Puche J, Barany G,. On-resin native chemical ligation for cyclic peptide synthesis. J. Org. Chem. 2004; 69: 4101-4107.
18. Ollivier N, Behr JB, 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.
19. α-9-fluorenylmethoxycarbonyl (Fmoc) chemistry: considerations of side-chain and backbone anchoring strategies, and compatible protection for N-terminal cysteine. J. Pept. Res. 2005; 65: 395-410.
20. 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.
21. Ohta Y, Itoh S, Shigenaga A, Shintaku S, Fujii N, Otaka A,. Cysteine-derived S-protected oxazolidinones: potential chemical devices for the preparation of peptide thioesters. Org. Lett. 2006; 8: 467-470.
22. Swinnen D, Hilvert D,. Facile, Fmoc-compatible solid-phase synthesis of peptide C-terminal thioesters. Org. Lett. 2000; 2: 2439-2442.
23. Quaderer R, Hilvert D,. Improved synthesis of C-terminal peptide thioesters on "safety-catch" resins using LiBr/THF. Org. Lett. 2001; 3: 3181-3184.
24. Sewing A, Hilvert D,. Fmoc-compatible solid-phase peptide synthesis of long C-terminal peptide thioesters. Angew. Chem. Int. Ed. 2001; 40: 3395-3396.
25. Nagaike F, Onuma Y, Kanazawa C, Hojo H, Ueki A, Nakahara Y, Nakahara Y,. Efficient microwave-assisted tandem N- to S-acyl transfer and thioester exchange for the preparation of a glycosylated peptide thioester. Org. Lett. 2006; 8: 4465-4468.
26. Blanco-Canosa JB, Dawson PE,. An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation. Angew. Chem. Int. Ed. 2008; 47: 6851-6855.
27. Mende F, Beisswenger M, Seitz O,. Automated Fmoc-based solid-phase synthesis of peptide thioesters with self-purification effect and application in the construction of immobilized SH3 domains. J. Am. Chem. Soc. 2010; 132: 11110-11118.
28. Tofteng AP, Sørensen KK, Conde-Frieboes KW, Hoeg-Jensen T, Jensen KJ,. Fmoc solid-phase synthesis of C-terminal peptide thioesters by formation of a backbone pyroglutamyl imide moiety. Angew. Chem. Int. Ed. 2009; 48: 7411-7414.
29. 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.
30. Hojo H, Onuma Y, Akimoto Y, Nakahara Y, Nakahara Y,. N-Alkyl cysteine-assisted thioesterification of peptides. Tetrahedron Lett. 2007; 48: 25-28.
31. Nakamura K, Mori H, Kawakami T, Hojo H, Nakahara Y, Aimoto S,. Peptide thioester synthesis via an auxiliary-mediated N-S acyl shift reaction in solution. Int. J. Pep. Res. Ther. 2007; 13: 191-202.
32. Nakamura K, Kanao T, Uesugi T, Hara T, Sato T, Kawakami T, Aimoto S,. Synthesis of peptide thioesters via an N-S acyl shift reaction under mild acidic conditions on an N-4,5-dimethoxy-2-mercaptobenzyl auxiliary group. J. Pept. Sci. 2009; 15: 731-737.
33. Tsuda S, Shigenaga A, Bando K, Otaka A,. N,S Acyl-transfer-mediated synthesis of peptide thioesters using anilide derivatives. Org. Lett. 2009; 11: 823-826.
34. Ollivier N, Dheur J, Mhidia R, Blanpain A, Melnyk O,. Bis(2-sulfanylethyl)amino native peptide ligation. Org. Lett. 2010; 12: 5238-5241.
35. Hou W, Zhang X, Li F, Liu CF,. Peptidyl N,N-bis(2-mercaptoethyl)-amides as thioester precursors for native chemical ligation. Org. Lett. 2011; 13: 386-389.
36. Taichi M, Hemu X, Qiu Y, Tam JP,. A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift. Org. Lett. 2013; 15: 2620-2623.
37. Boll E, Dheur J, Drobecq H, Melnyk O,. Access to cyclic or branched peptides using bis(2-sulfanylethyl)amido side-chain derivatives of Asp and Glu. Org. Lett. 2012; 14: 2222-2225.
38. Dheur J, Ollivier N, Vallin A, Melnyk O,. Synthesis of peptide alkylthioesters using the intramolecular N,S-acyl shift properties of bis(2-sulfanylethyl)amido peptides. J. Org. Chem. 2011; 76: 3194-3202.
39. Dheur J, Ollivier N, Melnyk O,. Synthesis of thiazolidine thioester peptides and acceleration of native chemical ligation. Org. Lett. 2011; 13: 1560-1563.
40. Pira SL, Boll E, Melnyk O,. Synthesis of peptide thioacids at neutral pH using bis(2-sulfanylethyl)amido peptide precursors. Org. Lett. 2013; 15: 5346-5349.
41. Ollivier N, Vicogne J, Vallin A, Drobecq H, Desmet R, El-Mahdi O, Leclercq B, Goormachtigh G, Fafeur V, Melnyk O,. A one-pot three-segment ligation strategy for protein chemical synthesis. Angew. Chem. Int. Ed. 2012; 51: 209-213.
42. Ancot F, Leroy C, Muharram G, Lefebvre J, Vicogne J, Lemiere A, Kherrouche Z, Foveau B, Pourtier A, Melnyk O, Giordano S, Chotteau-Lelievre A, Tulasne D,. Shedding-generated Met receptor fragments can be routed to either the proteasomal or the lysosomal degradation pathway. Traffic 2012; 13: 1261-1272.
43. Raibaut L, Vicogne J, Leclercq B, Drobecq H, Desmet R, Melnyk O,. Total synthesis of biotinylated N domain of human hepatocyte growth factor. Bioorg. Med. Chem. 2013; 21: 3486-3494.
44. Dang B, Kubota T, Mandal K, Bezanilla F, Kent SB,. Native chemical ligation at Asx-Cys, Glx-Cys: chemical synthesis and high-resolution X-ray structure of ShK toxin by racemic protein crystallography. J. Am. Chem. Soc. 2013; 135: 11911-11919.
45. Raibaut L, Seeberger P, Melnyk O,. Bis(2-sulfanylethyl)amido peptides enable native chemical ligation at proline and minimize deletion side-product formation. Org. Lett. 2013; 15 (21): 5516-5519.
46. Banerjee SR, Maresca KP, Stephenson KA, Valliant JF, Babich JW, Graham WA, Barzana M, Dong Q, Fischman AJ, Zubieta J,. N,N-bis(2-mercaptoethyl) methylamine a new coligand for Tc-99m labeling of hydrazinonicotinamide peptides. Bioconj. Chem. 2005; 16: 885-902.
47. Vojkovsky T,. Detection of secondary amines on solid phase. Pept. Res. 1995; 8: 236-237.