Abstract
Microwave technology, in conjunction with the isopeptide strategy including Fmoc-based solid-phase peptide synthesis (SPPS), was used to establish a methodology for time-efficient synthesis of peptides containing difficult sequences. A model difficult sequence-containing peptide (8QSer) was synthesized through this method in 1 day, representing a tenfold reduction in synthesis time compared to the isopeptide method combined with classical SPPS.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Merrifield RB (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 85:2149–2154
Albericio F (2004) Developments in peptide and amide synthesis. Curr Opin Chem Biol 8:211–221
Coin I, Beyermann M, Bienert M (2007) Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences. Nat Protoc 2:3247–3256
Katritzky AR, Haase DN, Johnson JV, Chung A (2009) Benzotriazole-assisted solid-phase assembly of Leu-enkephalin, amyloid β segment 34-42, and other “Difficult” peptide sequences. J Org Chem 74:2028–2032
Milton RCL, Milton SCF, Adams PA (1990) Prediction of difficult sequences in solid-phase peptide synthesis. J Am Chem Soc 112:6039–6046
Hyde C, Johnson T, Owen D, Quibell M, Sheppard RC (1994) Some “difficult sequences” made easy. A study of interchain association in solid-phase peptide synthesis. Int J Pept Protein Res 43:431–440
Yoshiya T, Taniguchi A, Sohma Y et al (2007) O-acyl isopeptide method for peptide synthesis: synthesis of forty kinds of “O-acyl isodipeptide unit” Boc-Ser/Thr(Fmoc-Xaa)-OH. Org Biomol Chem 5:1720–1730
Chou PY, Fasman GD (1978) Prediction of the secondary structure of proteins from their amino acid sequence. Adv Enzymol Relat Areas Mol Biol 47:45–148
Levitt M (1978) Conformational preferences of amino acids in globular proteins. Biochemistry 17:4277–4285
Blaakmeer J, Tijsse-Klasen T, Tesser GI (1991) Enhancement of solubility by temporary dimethoxybenzyl-substitution of peptide bonds. Towards the synthesis of defined oligomers of alanine and of lysyl-glutamyl-glycine. Int J Pept Protein Res 37:556–564
Toniolo C, Bonora GM, Mutter M, Pillai VNR (1981) Linear oligopeptides. 78. Effect of the insertion of a proline residue on the solution conformation of host peptides. Makromol Chem 182:2007–2014
Sohma Y, Sasaki M, Hayashi Y, Kimura T, Kiso Y (2004) Novel and efficient synthesis of difficult sequence-containing peptides through O-N intramolecular acyl migration reaction of O-acyl isopeptides. Chem Commun 1:124–125
Sohma Y, Taniguchi A, Yoshiya T et al (2006) Click peptide: a novel O-acyl isopeptide method for peptide synthesis and chemical biology-oriented synthesis of amyloid β peptide analogues. J Pept Sci 12:823–828
Sohma Y, Hayashi Y, Skwarczynski M et al (2004) O-N intramolecular acyl migration reaction in the development of prodrugs and the synthesis of difficult sequence-containing bioactive peptides. Biopolymers 76:344–356
Sohma Y, Yoshiya T, Taniguchi A, Kimura T, Hayashi Y, Kiso Y (2007) Development of O-acyl isopeptide method. Biopolymers 88:253–262
Sohma Y, Taniguchi A, Skwarczynski M et al (2006) O-Acyl isopeptide method' for the efficient synthesis of difficult sequence-containing peptides: use of O-acyl isodipeptide unit. Tetrahedron Lett 47:3013–3017
Sohma Y, Sasaki M, Hayashi Y, Kimura T, Kiso Y (2004) Design and synthesis of a novel water-soluble Aβ1-42 isopeptide: an efficient strategy for the preparation of Alzheimer's disease-related peptide, Aβ1-42, via O-N intramolecular acyl migration reaction. Tetrahedron Lett 45:5965–5968
Carpino LA, Krause E, Sferdean CD et al (2004) Synthesis of “difficult” peptide sequences: application of a depsipeptide technique to the Jung-Redemann 10- and 26-mers and the amyloid peptide Aβ(1-42). Tetrahedron Lett 45:7519–7523
Coin I, Doelling R, Krause E et al (2006) Depsipeptide methodology for solid-phase peptide synthesis: circumventing side reactions and development of an automated technique via depsidipeptide units. J Org Chem 71:6171–6177
Mutter M, Chandravarkar A, Boyat C et al (2004) Switch peptides in statu nascendi: induction of conformational transitions relevant to degenerative diseases. Angew Chem Int Ed 43:4172–4178
Skwarczynski M, Kiso Y (2007) Application of the O-N intramolecular acyl migration reaction in medicinal chemistry. Curr Med Chem 14:2813–2823
Skwarczynski M, Sohma Y, Noguchi M, Kimura T, Hayashi Y, Kiso Y (2006) O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids. J Org Chem 71:2542–2545
Sohma Y, Chiyomori Y, Kimura M et al (2005) O-Acyl isopeptide method' for the efficient preparation of amyloid β peptide 1-42 mutants. Bioorg Med Chem 13:6167–6174
Sohma Y, Hayashi Y, Kimura M et al (2005) The “O-acyl isopeptide method” for the synthesis of difficult sequence-containing peptides: application to the synthesis of Alzheimer’s disease-related amyloid β peptide (Aβ) 1-42. J Pept Sci 11:441–451
Taniguchi A, Skwarczynski M, Sohma Y et al (2008) Controlled production of amyloid β peptide from a phototriggered, water-soluble precursor click peptide. Chembiochem 9:3055–3065
Leadbeater NE, Torenius HM (2002) A study of the ionic liquid mediated microwave heating of organic solvents. J Org Chem 67:3145–3148
Stadler A, Kappe CO (2001) High-speed couplings and cleavages in microwave-heated, solid-phase reactions at high temperatures. Eur J Org Chem 2001:919–925
Stadler A, Kappe CO (2001) The effect of microwave irradiation on carbodiimide-mediated esterification on solid support. Tetrahedron 57:3915–3920
Erdelyi M, Gogoll A (2002) Rapid microwave-assisted solid phase peptide synthesis. Synthesis 11:1592–1596
Murray JK, Gellman SH (2007) Parallel synthesis of peptide libraries using microwave irradiation. Nat Protoc 2:624–631
Olivos HJ, Alluri PG, Reddy MM, Salony D, Kodadek T (2002) Microwave-assisted solid-phase synthesis of peptoids. Org Lett 4:4057–4059
Park M-S, Oh H-S, Cho H, Lee K-H (2007) Microwave-assisted solid-phase synthesis of pseudopeptides containing reduced amide bond. Tetrahedron Lett 48:1053–1057
Pedersen SL, Tofteng AP, Malik L, Jensen KJ (2012) Microwave heating in solid-phase peptide synthesis. Chem Soc Rev 41:1826–1844
Pedersen SL, Soerensen KK, Jensen KJ (2010) Semi-automated microwave-assisted SPPS: optimization of protocols and synthesis of difficult sequences. Biopolymers 94:206–212
Hussein WM, Liu T-Y, Toth I, Skwarczynski M (2013) Microwave-assisted synthesis of difficult sequence-containing peptides using the isopeptide method. Org Biomol Chem 11:2370–2376
Palasek SA, Cox ZJ, Collins JM (2007) Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J Pept Sci 13:143–148
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2020 Springer Science+Business Media, LLC, part of Springer Nature
About this protocol
Cite this protocol
Hussein, W.M., Skwarczynski, M., Toth, I. (2020). An Isodipeptide Building Block for Microwave-Assisted Solid-Phase Synthesis of Difficult Sequence-Containing Peptides. In: Hussein, W., Skwarczynski, M., Toth, I. (eds) Peptide Synthesis. Methods in Molecular Biology, vol 2103. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-0227-0_9
Download citation
DOI: https://doi.org/10.1007/978-1-0716-0227-0_9
Published:
Publisher Name: Humana, New York, NY
Print ISBN: 978-1-0716-0226-3
Online ISBN: 978-1-0716-0227-0
eBook Packages: Springer Protocols