Synthesis of peptide aldehydes

Journal of Peptide Science

Volumn 13, Issue 1, 2007, Pages 1-15

  Moulin, Aline ^a   Martinez, Jean ^a   Fehrentz, Jean Alain ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Epimerization; Peptide aldehydes; SPPS; Synthesis in solution

Indexed keywords

ALDEHYDE; ALKENE; AMINO ACID; ARGININE; CASPASE INHIBITOR; INTERLEUKIN 1BETA CONVERTING ENZYME INHIBITOR; MORPHOLINE; PEPTIDE ALDEHYDE; SERINE PROTEINASE INHIBITOR; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

CARBOXY TERMINAL SEQUENCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; OXIDATION; PEPTIDE SYNTHESIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN FUNCTION; PROTEIN MODIFICATION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; RESIDUE ANALYSIS; REVIEW; SAPONIFICATION; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ALDEHYDES; ALKENES; AMINO ACID SEQUENCE; ARGININE; ASPARTIC ACID; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM;

EID: 33846652279     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.787     Document Type: Review

References (53)

1. Jacobson KA, Marr-Leisy D, Rosenkranz RP, Verlander MS, Melmon KL, Goodman M. Conjugates of catecholamines. 1. N-Alkyl-functionalized carboxylic acid congeners and amides related to isoproterenol. J. Med. Chem. 1983; 26: 492-499.
2. Spetzler JC, Tam JP. Unprotected peptides as building blocks for branched peptides and peptide dendrimers. Int. J. Pept. Protein Res. 1995; 45: 78-85.
3. Tam JP, Rao C, Liu C-F, Shao J. Specificity and formation of unusual amino acids of an amide ligation strategy for unprotected peptides. Int. J. Pept. Protein Res. 1995; 45: 209-216.
4. Canne LE, Ferre- D'Amare AR, Burley SK, Kent SBH. Total chemical synthesis of a Unique transcription factor-related protein: cMyc-max. J. Am. Chem. Soc. 1995: 117: 2998-3007.
5. Rose K. Facile synthesis of homogeneous artificial proteins. J. Am. Chem. Soc. 1994: 116: 30-33.
6. King TP, Zhao SW, Lam T. Preparation of protein conjugates via intermolecular hydrazone linkage. Biochemistry 1986; 25: 5774-5779.
7. Aoyagi T, Takeuchi T, Matsuzaki A, Kawamura K, Kondo S, Hamada M, Maeda K, Umezawa H. Leupeptins, new protease inhibitors from actinomycetes. J. Antibiot. 1969; 22: 283-286.
8. Basak A, Jean F, Seidah NG, Lazure C. Design and synthesis of novel inhibitors of prohormone convertases. Int. J. Pept. Protein Res. 1994; 44: 253-261.
9. Sarubbi E, Seneci PF, Angelastro MR, Peet NP, Denaro M, Islam K. Peptide aldehydes as inhibitors of HIV protease. FEBS Lett. 1993; 319: 253-256.
10. Fehrentz J-A, Heitz A, Castro B, Cazaubon C, Nisato D. Aldehydic peptides inhibiting renin. FEBS Lett. 1984; 167: 273-276.
11. Fehrentz J-A, Heitz A, Castro B. Synthesis of aldehydic peptides inhibiting renin. Int. J. Pept. Protein Res. 1985: 26: 236-241.
12. Ganneau C, Moulin A, Demange L, Martinez J, Fehrentz J-A. The epimerization of peptide aldehydes - a systematic study. J. Pept. Sci. 2006; 12: 497-501.
13. Hamada Y, Shioiri T. New methods and reagents in organic synthesis. 29. A practical method for the preparation of optically active N-protected α-amino aldehydes and peptide aldehydes. Chem. Pharm. Bull. 1982; 30: 1921-1924.
14. Sorg G, Thern B, Mader O, Rademann J, Jung G. Progress in the preparation of peptide aldehydes via polymer supported IBX oxidation and scavenging by threonyl resin. J. Pept. Sci. 2005; 11: 142-152.
15. Guichard G, Briand JP, Friede M. Synthesis of arginine aldehydes for the preparation of pseudopeptides. Pept. Res. 1993: 6: 121-124.
16. Fehrentz J-A, Paris M, Heitz A, Velek J, Liu C-F, Winternitz F, Martinez J. Improved solid phase synthesis of C-terminal peptide aldehydes. Tetrahedron Lett. 1995; 36: 7871-7874.
17. Tong XH, Hong A. Solid phase synthesis of aspartyl peptide aldehydes. Tetrahedron Lett. 2000; 41: 8857-8860.
18. Higaki JN, Chakravarty S, Bryant CM, Cowart LR, Harden P, Scardina JM, Mavunkel B, Luedtke GR, Cordell B. A combinatorial approach to the identification of dipeptide aldehyde inhibitors of β-amyloid production. J. Med. Chem. 1999; 42: 3889-3898.
19. Salvino JM, Mervic M, Mason HJ, Kiesow T, Teager D, Airey J, Labaudiniere R. Parallel synthesis of aldehydes and ketone facilitated by a new solid-phase Weinreb amide. J. Org. Chem. 1999; 64: 1823-1830.
20. Nahm S, Weinreb SM. N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett. 1981; 22: 3815-3818.
21. Douat C, Heitz A, Martinez J, Fehrentz J-A. Synthesis of N-protected α-amino aldehydes from their morpholine amide derivatives. Tetrahedron Lett. 2000; 41: 37-40.
22. Zlatoidsky P. Preparation of Boc-amino-acid or peptide aldehydes via reduction of corresponding phenyl esters. Helv. Chim. Acta 1994; 77: 150-154.
23. Fuller WD, Cohen MP, Shabankareh M, Blair RK, Goodman M, Naider FR. Urethane protected amino acid N-carboxyanhydrides and their use in peptide synthesis. J. Am. Chem. Soc. 1990; 112: 7414-7416.
24. Xue CB, Naider F. Application of N-(tert-butyloxycarbonyl)amino acid N-carboxyanhydrides in solid-phase peptide synthesis. J. Org. Chem. 1993; 58: 350-355.
25. Chevallet P, Fehrentz J-A, Kiec-Kononowicz K, Devin C, Castel J, Loffet A, Martinez J. Synthesis of chiral N-protected amino acid esters by the use of UNCAs. Lett. Pept. Sci. 1996; 2: 297-300.
26. Fehrentz J-A, Paris M, Heitz A, Velek J, Winternitz F, Martinez J. Solid phase synthesis of C-Terminal peptide aldehydes. J. Org. Chem. 1997; 62: 6792-6796.
27. Wyslouch-Cieszynska A, Tam PT. In Peptides: Frontiers of Peptide Science, Proceedings of the Fifteenth American Peptide Symposium, Tam PJ, Kaumaya PTP (eds). Kluwer Academic Publishers; The Netherlands, Dordrecht, 1999; 263-264.
28. Galeotti N, Giraud M, Jouin P. Solid phase synthesis of peptidyl aldehydes from C-terminal thiazolidinyl peptides. Lett. Pept. Sci. 1997; 4: 437-440.
29. Yde B, Yousif NM, Pedersen U, Thomsen I, Lawesson SO. Studies on organophosphorus compounds. XLVII. Preparation of thiated synthons of amides, lactams and imides by use of some new phosphorus- and sulfur-containing reagents. Tetrahedron 1984; 40: 2047-2052.
30. Dondoni A, Marra A, Perrone D. Efficacious modification of the procedure for the aldehyde release from 2-substituted thiazoles. J. Org. Chem. 1993; 58: 275-277.
31. Garrett GS, Correa PE, McPhail SJ, Tornheim K, Burton JA, Eickhoff DJ, Engerholm GG, McIver JM. Peptide aldehyde inhibitors of the kallikreins: an investigation of subsite interactions with tripeptides containing structural variations at the amino terminus. J. Pept. Res. 1998; 52: 60-71.
32. Murphy AM, Dagnino R Jr, Vallar PL, Trippe AJ, Sherman SL, Lumpkin RH, Tamura SY, Webb TR. Automated synthesis of peptide C-terminal aldehydes. J. Am. Chem. Soc, 1992; 114: 3156-3157.
33. Dagnino R Jr, Webb TR. Improved synthesis of arginine peptide aldehydes. Tetrahedron Lett. 1994; 35: 2125-2128.
34. Linton SD, Karanewsky DS, Ternansky RJ, Wu JC, Pham B, Kodandapani L, Smidt R, Diaz J-L, Fritz LC, Tomaselli KJ. Acyl dipeptides as reversible caspase inhibitors. Part 1: initial lead optimization. Bioorg. Med. Chem. Lett. 2002; 12: 2969-2971.
35. Ramage R, Irving SL, McInnes C. Design of a versatile linker for solid phase peptide synthesis: synthesis of C-terminal primary/secondary amides and hydrazides. Tetrahedron Lett. 1993; 34: 6599-6602.
36. Patterson JA, Ramage R. Solid phase synthesis of peptide C-terminal semicarbazones and aldehydes. Tetrahedron Lett. 1999; 40: 6121-6124.
37. Ede NJ, Bray AM. A simple linker for the attachment of aldehydes to the solid phase. Application to solid phase synthesis by the Multipin method. Tetrahedron Lett. 1997; 38: 7119-7122.
38. Gros C, Boulegue C, Galeotti N, Niel G, Jouin P. Stereochemical control in the preparation of α-amino N-methylthiazolidine masked aldehydes used for peptide aldehydes synthesis. Tetrahedron 2002; 58: 2673-2680.
39. Pothion C, Paris M, Heitz A, Rocheblave L, Rouch F, Fehrentz J-A, Martinez J. Use of ozonolysis in the synthesis of C-terminal peptide aldehydes on solid support. Tetrahedron Lett. 1997; 38: 7749-7752.
40. Schuerch C, Frechet JM. Solid-phase synthesis of oligosaccharides. I. Preparation of the solid support. Poly[p-(1-propen-3-ol-1-yl)styrene]. J. Am. Chem. Soc. 1971: 93: 492-496.
41. Hodge P, Waterhouse J. Chemical modification of chloromethylated crosslinked polystyrene via phase transfer catalyzed Wittig reactions. Polymer 1981: 22: 1153-1154.
42. Paris M, Heitz A, Guerlavais V, Cristau M, Fehrentz J-A, Martinez J. Synthesis of peptide aldehydes on solid support using ozonolysis. Tetrahedron Lett. 1998; 39: 7287-7290.
43. Hird NW, Irie K, Nagai K. Solid phase synthesis of 2-aminobutadienes using a piperazine linker. Tetrahedron Lett. 1997; 38: 7111-7114.
44. Hall BJ, Sutherland JD. A practical method for the combinatorial synthesis of peptide aldehydes. Tetrahedron Lett. 1998; 39: 6593-6596.
45. Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masamune S, Roush WR, Sakai T. Horner-Wadsworth-Emmons reaction: use of lithium chloride and an amine for base-sensitive compounds. Tetrahedron Lett. 1984; 25: 2183-2186.
46. Jensen KJ, Alsina. J, Songster MF, Vagner J, Albericio F, Barany G. Backbone amide linker strategy for solid-phase synthesis of C-Terminal-modified and cyclic peptides. J. Am. Chem. Soc. 1998: 120: 5441-5452.
47. Kappel JC, Barany G. Backbone amide linker (BAL) strategy for Nα-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of peptide aldehydes. J. Pept. Sci. 2005; 11: 525-535.
48. Tamura SY, Semple JE, Ardecky RJ, Leon P, Carpenter SH, Ge Y, Shamblin BM, Weinbouse MI, Ripka WC, Nutt RF. Novel and general method for the preparation of peptidyl argininals. Tetrahedron Lett. 1996; 37: 4109-4112.
49. Siev DV, Gaudette JA, Semple JE. Novel protocol for the solid-phase synthesis of peptidyl and peptidomimetic Pl-argininal derivatives. Tetrahedron Lett. 1999; 40: 5123-5127.
50. Chapman KT. Synthesis of a potent, reversible inhibitor of interleukin-1β converting enzyme. Bioorg. Med. Chem. Lett. 1992; 2: 613-618.
51. Mancuso AJ, Huang S-L, Swern D. Oxiddation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide activated by oxalyl chloride. J. Org. Chem, 1978; 43: 2480-2482.
52. Dangles O, Guibe F, Balavoine G, Lavielle S, Marquet A. Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis, J. Org. Chem. 1987; 52: 4984-4993.
53. Graybill TL, Dolle RE, Helaszek CT, Miller RE, Ator MA. Preparation and evaluation of peptidic aspartyl hemiacetals as reversible inhibitors of interleukin-1β converting enzyme (ICE). Int. J. Pept. Protein Res. 1994; 44: 173-182.