Developments in peptide and amide synthesis

Current Opinion in Chemical Biology

Volumn 8, Issue 3, 2004, Pages 211-221

  Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

native chemical ligation; NCL; solid phase peptide synthesis; SPPS

Indexed keywords

ALANINE; AMIDE; AMINO ACID; ASPARAGINE; CARBOXYLIC ACID; CHLORIDE; CYCLOSPORIN; CYSTEINE; ENFUVIRTIDE; FLUORIDE; GLUTAMIC ACID; GLUTAMINE; GUANIDINE; HISTIDINE; LYSINE; MAJOR HISTOCOMPATIBILITY ANTIGEN CLASS 2; PEPTIDE; PHENYLALANINE; SERINE; THREONINE; TYROSINE;

AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; CARBOXY TERMINAL SEQUENCE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHIRALITY; GEL FILTRATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGATION; MOLECULAR SIZE; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; RACEMIZATION; REVIEW; SOLID STATE;

AMIDES; AMINO ACIDS; CHEMISTRY, ORGANIC; CROSS-LINKING REAGENTS; MODELS, CHEMICAL; PEPTIDES; PEPTIDES, CYCLIC; RESINS, PLANT;

EID: 2942567819     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2004.03.002     Document Type: Review

References (41)

1. Lloyd-Williams P, Albericio F, Giralt E: Chemical Approaches to the Synthesis of Peptides and Proteins. Boca Raton, Florida: CRC; 1997.
2. Albericio F., Chinchilla R., Dodsworth D.J., Najera C. New trends in peptide coupling reagents. Org Prep Proced Int. 33:2001;203-303
3. Carpino L, El-Faham A, Minor CA, Albericio F: Advantageous applications of azabenzotriazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis. Chem Comm 1994:201-203.
4. Sabatino G., Mulinacci B., Alcaro M.C., Chelli M., Rovero P., Papini A.M. Assessment of new 6-Cl-HOBt based coupling reagents for peptide synthesis. Part 1: Coupling efficiency study. Lett Peptide Sci. 9:2003;119-123
5. Carpino L.A., Xia J., El-Faham A. 3-Hydroxy-4-oxo-3, 4-dihydro-5- azabenzo-1, 2, 3-triazene. J Org Chem. 69:2004;54-61 Active esters of the reagent described in the article is slightly more reactive even than the OAt esters, which are considered the most reactive derivatives among these esters.
6. Li H., Jiang X., Ye Y.-H., Fan C., Romoff T., Goodman M. 3-(Diethoxyphosphoryloxy)-1, 2, 3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization. Org Lett. 1:1999;91-93
7. 2.
8. Alsina J., Jensen K.J., Albericio F., Barany G. Solid-phase synthesis with tris(alkoxy)benzyl backbone amide linkage (BAL). Chem Eur J. 5:1999;2787-2795
9. Thern B., Rudolph J., Jung G. Total synthesis of the nematicidal cyclododecapeptide omphalotin A by using racemization-free triphosgene-mediated couplings in the solid phase. Angew Chem Int Ed. 41:2002;2307-2309
10. Falb E., Yechezkel T., Salitra Y., Gilon C. In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis. J Peptide Res. 53:1999;507-517
11. Carpino L.A., El-Faham A. The diisopropylcarbodiimide/1-hydroxy-7- azabenzotriazole system: segment coupling and stepwise peptide assembly. Tetrahedron. 55:1999;6813-6830
12. Carpino L.A., El-Faham A. Tetramethylfluoroformamidinium hexafluorophosphate: a rapid-acting peptide coupling reagent for solution and solid phase peptide synthesis. J Am Chem Soc. 117:1995;5401-5402
13. Carpino L.A., Ionescu D., El-Faham A., Beyermann M., Henklein P., Hanay C., Wenschuh H., Bienert M. Complex polyfluoride additives in Fmoc-amino acid fluoride coupling processes. Enhanced reactivity and avoidance of stereomutation. Org Lett. 5:2003;975-977 The addition of the relatively cheap polyfluoride additives leads to an increase in the reactivity and a reduction in the loss chirality for other coupling methods.
14. Barlos K., Gatos D., Kallitsis J., Papaphotiu G., Sotiriu P., Yao W., Schaefer W. Preparation of protected peptide fragments using triphenylmethyl resins. Tetrahedron Lett. 30:1989;3943-3946
15. Albericio F., Cruz M., Debethune L., Eritja R., Giralt E., Grandas A., Marchan V., Pastor J.J., Pedroso E., Rabanal F., Royo M. An improved synthesis of N-[9-hydroxymethyl)-2-fluorenyl]succinamic acid (HMES), a versatile handle for the solid-phase synthesis of biomolecules. Synthetic Comm. 31:2001;225-232
16. Alsina J., Albericio F. Solid-phase synthesis of C-terminal modified peptides. Biopolymers. 71:2003;454-477 A report on methods for solid-phase synthesis of C-terminal modified peptides as well as general information about biological activities and/or synthetic applications of each individual class of peptide.
17. Bernhardt A., Drewello M., Schutkowski M. The solid-phase synthesis of side-chain-phosphorylated peptide-4-nitroanilides. J Peptide Res. 50:1997;143-152
18. García O., Nicolás E., Albericio F. Solid-phase synthesis: a linker for side-chain anchoring of arginine. Tetrahedron Lett. 44:2003;5319-5321
19. Jiménez J.C., Chavarria B., López-Macià A., Royo M., Giralt E., Albericio F. Tentoxin as a scaffold for drug discovery. Total solid-phase synthesis of tentoxin and a library of analogues. Org Lett. 5:2003;2115-2118
20. Gu W., Silverman R.B. Solid-phase total synthesis of scytalidamide A. J Org Chem. 68:2003;8774-8779
21. Chiva C., Barthe P., Codina A., Gairi M., Molina F., Granier C., Pugniere M., Inui T., Nishi H., Nishiuchi Y., Kimura T., Sakakibara S., Albericio F., Giralt E. Synthesis and NMR structure of P41icf, a potent inhibitor of human cathepsin L. J Am Chem Soc. 125:2003;1508-1517 This and [19, 20] show representative examples of the state of the art in peptide synthesis.
22. Bray B.L. Innovation: large-scale manufacture of peptide therapeutics by chemical synthesis. Nature Rev Drug Discovery. 2:2003;587-593 The large-scale commercial production of a 36 amino acid peptides by chemical synthesis is demonstrated in the development of T-20. The rationale behind route selection and the scale-up of the process used to manufacture T-20 is discussed.
23. Nisiuchi Y., Inui T., Nishio H., Bodi J., Kimura T., Tsuji F.T., Sakakibara S. Chemical synthesis of the precursor molecule of the aequorea green fluorescent protein, subsequent folding, and development of fluorescence. Proc Natl Acad Sci USA. 95:1998;13549-13554
24. Dawson P: Chemical ligation. In Houben-Weyl, Methods of Organic Chemistry, V. E22a, Synthesis of Peptides and Peptidomimetics. Edited by Goodman M, Felix A, Moroder L, Toniolo C. New York: Thieme Stuttgart; 2002:627-641.
25. Kent S. Total chemical synthesis of enzymes. J Peptide Sci. 9:2003;574-593 Modern chemical ligation methods allow the preparation of protein and enzymes.
26. Tam J.P., Xu J., Eom K.D. Methods and strategies of peptide ligation. Biopolymers. 60:2001;194-205
27. Shin Y., Winans K.A., Backes B.J., Kent S.B.H., Ellman J.A., Bertozzi C.R. Fmoc-based synthesis of peptide-αthioesters: application to the total chemical synthesis of a glycoprotein by native chemical ligation. J Am Chem Soc. 121:1999;11684-11689
28. 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. 121:1999;11369-11374
29. Alsina J., Yokum T.S., Albericio F., Barany G. Backbone amide linker (BAL) strategy for Nα-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters. J Org Chem. 64:1999;8761-8769
30. Brask J., Albericio F., Jensen K.J. Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters. Org Lett. 5:2003;2951-2953 Backbone strategy for the preparation of thioester peptides using Fmoc chemistry in which the thioester functionality is masked as a trithioortho ester throughout the synthesis.
31. Tam J.P., Yu Q. Methionine ligation strategy in the biomimetic synthesis of parathyroid hormones. Biopolymers. 46:1998;319-327
32. Yan L.Z., Dawson P.E. Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization. J Am Chem Soc. 123:2001;526-533
33. Clive D.L.J., Hisaindee S., Coltart D.M. Derivatized amino acids relevant to native peptide synthesis by chemical ligation and acyl transfer. J Org Chem. 68:2003;9247-9254
34. Canne L.E., Bark S.J., Kent S.B.H. Extending the applicability of native chemical ligation. J Am Chem Soc. 118:1996;5891-5896
35. Vizzavona J., Dick F., Vorherr T. Synthesis and application of an auxiliary group for chemical ligation at the X-gly site. Bioorg Med Chem Lett. 12:2002;1963-1965
36. Offer J., Boddy C.N.C., Dawson P.E. Extending synthetic access to proteins with a removable acyl transfer auxiliary. J Am Chem Soc. 124:2002;4642-4646
37. Cardona V.M.F., Hartley O., Botti P. Synthesis of cyclic peptides from unprotected precursors using removable Nα-[1-(4-methoxyphenyl)-2- mercaptoethyl] auxiliary. J Peptide Res. 6:2003;152-157
38. Nilsson B.L., Hondal R.J., Soellner M.B., Raines R.T. Protein assembly by orthogonal chemical ligation methods. J Am Chem Soc. 125:2003;5268-5269 Staundinger native chemical ligation allows the preparation of proteins without the requirement of having a Cys residue as the N-terminal residue on the peptide to be coupled.
39. Toepert F., Knaute T., Guffler S., Pires J.R., Matzdorf T., Oschkinat H., Schneider-Mergener J. Combining SPOT synthesis and native peptide ligation to create large arrays of WW protein domains. Angew Chem Int Ed. 42:2003;1136-1140 Native chemical ligation allows an easy preparation of an array of 11 859 synthetic variants of the WW domain.
40. Kochendoerfer G.G., Chen S.-Y., Mao F., Cressman S., Traviglia S., Shao H., Hunter C.L., Low D.W., Cagle E.N., Carnevali M., et al. Design and chemical synthesis of a homogeneous polymer-modified erythropoiesis protein. Science. 299:2003;884-887 This paper describes how chemical methods are a powerful tool in the rational design of protein constructs with potential therapeutic applications.
41. Vallette H., Ferron L., Coquerel G., Gaumont A.-C., Plaquevent J.-C. Peptide synthesis in room temperature ionic liquids. Tetrahedron Lett. 45:2004;1617-1619 The use of room temperature ionic liquids for coupling, a green chemistry method, opens the possibility of using that chemistry for peptide synthesis.