Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy. III: Racemization studies and water-based synthesis of histidine-containing peptides

Amino Acids

Volumn 46, Issue 10, 2014, Pages 2347-2354

  Hojo, Keiko ^a,b   Shinozaki, Natsuki ^a   Hidaka, Koushi ^a   Tsuda, Yuko ^a   Fukumori, Yoshinobu ^a   Ichikawa, Hideki ^a   Wade, John D ^b  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Histidine; Microwave assisted synthesis; Nanoparticles; Racemization; Solid phase peptide synthesis; Synthesis in water

Indexed keywords

4-(4,6-DIMETHOXY-1,3,5-TRIAZIN-2-YL)-4-METHYLMORPHOLINIUM CHLORIDE; AMINO ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORENE DERIVATIVE; HISTIDINE; MORPHOLINE DERIVATIVE; N(ALPHA)-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS; NANOPARTICLE; NEUROPEPTIDE; NPW PROTEIN, HUMAN; OLIGOPEPTIDE; PEPTIDE FRAGMENT; TYROSYL-HISTIDYL-THREONYL-VALYL-GLYCYL-ARGININAMIDE;

ANIMAL; CHEMISTRY; GREEN CHEMISTRY; MICROWAVE RADIATION; RAT; SOLID PHASE SYNTHESIS; SOLUBILITY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; ANIMALS; FLUORENES; GREEN CHEMISTRY TECHNOLOGY; HISTIDINE; INDICATORS AND REAGENTS; MICROWAVES; MORPHOLINES; NANOPARTICLES; NEUROPEPTIDES; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; RATS; SOLID-PHASE SYNTHESIS TECHNIQUES; SOLUBILITY; STEREOISOMERISM;

EID: 84930709714     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-014-1779-y     Document Type: Article

References (43)

1. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, New York
2. Angeletti RH, Bibbs L, Bonewald LF, Fields GB, Kelly JW, McMurray JS, Moore WT, Weintraub ST (1997) Analysis of racemization during "standard" solid phase peptide synthesis: a multicenter study. In: Marshak DR (ed) Techniques in protein chemistry III. Academic Press Inc, San Diego, pp 875-890
3. Angell YM, Alsina J, Albericio F, Barany G (2002) Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides. J Pept Res 60:292-299
4. Bodanszky M, Bodanszky A (1967) Racemization in peptide chemistry. Mechanism-specific models. Chem Commun 1967:591-592
5. Collins JM, Collin MJ (2003) Novel method for enhanced solid-phase peptide synthesis using microwave energy. Biopolymers 71:361-366
6. Dourtoglou V, Ziegler JC, Gross B (1978) L'hexafluorophosphate de O-benzotriazoyl- N, N, N', N'-tetramethyluronium: un reactif de couplage peptidique nouveau et efficace. Tetrahedron Lett 19:1269-1272
7. Dourtoglou V, Gross B, Lambropoulou C, Ziodrou C (1984) O-Benzotriazolyl-N, N, N', N'-tetramethyluronium hexafluorophosphate as coupling reagent for the synthesis of peptides of biological interest. Synthesis 1984:572-574
8. Echalier C, Ai-Halifa S, Kreiter A, Enjalbal C, Sanchez P, Ronga L, Puget K, Verdié P, Amblard M, Martinez J, Subra G (2013) Heating and microwave assisted SPPS of C-terminal acid peptides on trityl resin: the truth behind the yield. Amino Acids 45:1395-1403
9. Erdélyi M, Gogoll A (2002) Rapid microwave-assisted solid-phase peptide synthesis. Synthesis 11:1592-1596
10. π -phenacyl group for the protection of the histidine side chain in peptide synthesis. J Chem Soc Perkin Trans 1(1979):2261-2267
11. Friligou I, Papadimitriou E, Gatos D, Matsoukas J, Tselios T (2011) Microwave-assisted solid-phase peptide synthesis of the 60-110 domain of human pleiotrophin on 2-chlorotrityl resin. Amino Acids 40:1431-1440
12. Han Y, Albericio F, Barany G (1997) Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis. J Org Chem 62:4307-4312
13. π -protecting group for histidine to eliminate side-chain-induced racemization in the Fmoc strategy. Tetrahedron Lett 52:4947-4949
14. π -4-methoxybenzyloxymethylhistidine in solid phase peptide synthesis. J Pept Sci 18:763-769
15. Hojo K, Maeda M, Kawasaki K (2001) A new water-soluble N-protecting group, 2-[phenyl (methyl) sulfonio] ethyloxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water. J Pept Sci 7:615-618
16. Hojo K, Maeda M, Kawasaki K (2004a) A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to peptide synthesis. Tetrahedron 60:1875-1866
17. Hojo K, Maeda M, Kawasaki K (2004b) 2-(4-Sulfophenyl) ethoxycarbonyl group: a new water-soluble N-protecting group and its application to solid-phase peptide synthesis in water. Tetrahedron Lett 45:9293-9295
18. Hojo K, Ichikawa H, Maeda M, Kida S, Fukumori Y, Kawasaki K (2007) Solid-phase peptide synthesis using nanoparticulate amino acids in water. J PeptSci 13:493-497
19. Hojo K, Ichikawa H, Fukumori Y, Kawasaki K (2008) Development of a method for solid-phase peptide synthesis in water. Int J Pept Res Ther 14:373-380
20. Hojo K, Hara A, Kitai H, Onishi M, Ichikawa H, Fukumori Y, Kawasaki K (2011) Development of a method for environmentally friendly chemical peptide synthesis in water using water-dispersible amino acid nanoparticles. Chem Cent J 5:49
21. Hojo K, Ichikawa H, Hara A, Onishi M, Kawasaki K, Fukumori Y (2012) Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy: in-water synthesis of "difficult sequences". Protein Pept Lett 19:1231-1236
22. Hojo K, Ichikawa H, Hara A, Onishi M, Kawasaki K, Fukumori Y (2013) Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy II: racemization studies and water-based synthesis of cysteine-containing peptides. Protein Pept Lett 20:1122-1128
23. Isidro-Liobet A, Álavarez M, Albericio A (2009) Amino acid-protecting groups. Chem Rev 109:2455-2504
24. Jones JH, Ramage WI (1978) An approach to the prevention of racemization in the synthesis of histidine-containing peptides. J Chem Soc Chem Commun 1978:472-473
25. Kaiser E, Colescott RL, Bossinger CD, Cook PI (1970) Color test for detection of free terminal amino groups in the solid phase synthesis of peptide. Anal Biochem 1970:595-598
26. Kaiser T, Nicholson G, Kohlbau H, Volete R (1996) Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis. Tetrahedron Lett 37:1187-1190
27. Kaminski ZJ, Paneth P, Rudzinski JA (1998) Study on the activation of carboxylic acids by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 2-chloro-4,6-diphenoxy-1.3.5-triazine. J Org Chem 63:4248-4225
28. Kunishima M, Kawachi C, Morita J, Terao K, Iawasaki F, Tani S (1999) 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: an efficient condensing agent leading to the formulation of amide and esters. Tetrahedron 55:13159-13179
29. Loffrendo C, Assunção NA, Gerhardt J, Miranda MTM (2009) Microwave-assisted solid-phase peptide synthesis at 60 °C: alternative conditions with low enantiomerization. J Pept Sci 15:808-817
30. Mergler M, Dick F, Sax B, Schwindling J, Vorherr TH (2001) Synthesis of Fmoc-His(3-Bum)-OH. J Pept Sci 7:502-510
31. Olivos HJ, Alluri PG, Reddy MM, Salony D, Kodadek T (2002) Microwave-assisted solid-phase synthesis of peptides. Org Lett 4:4057-4059
32. Palasek SA, Cox ZJ, Collins LM (2007) Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J Pept Sci 13:143-148
33. Rabinow BE (2004) Nanosuspensions in drug delivery. Nat Rev Discov 3:785-795
34. Robertson N, Jiang L, Ramage R (1999) Racemisation studies of a novel reagent for solid-phase peptide synthesis. Tetrahedron 54:14233-14254
35. Sheehan JC, Hlavka JJ (1956) The use of water-soluble and basic carbodiimides in peptide synthesis. J Org Chem 21:439-441
36. Sheldon RA (2007) The E factor: fifteen years on. Green Chem 9:1273-1283
37. Shimomura Y, Harada M, Goto M, Sugo T, Matsumoto Y, Abe M, Watanabe T, Asami T, Kitada C, Mori M, Onda H, Fujino M (2002) Identification of neuropeptide W as the endogenous ligand for orphan G-protein-coupled receptors GPR7 amd GPR8. J Biol Chem 277:35826-35832
38. Sieber P, Riniker B (1978) Protection of histidine in peptide synthesis. A reassessment of the trityl group. Tetrahedron Lett 28:6031-6034
39. Staros JV, Wright RW, Swingle DM (1986) Enhancement by N-hydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions. Anal Biochem 156:220-222
40. Veber DF (1975) Peptide synthesis from the practitioner's point of view. In: Walter R, Meienhofer J (eds) Peptides: chemistry, structure and biology. Ann Arbor Science Publishers, Michigan, pp 307-316
41. Wade JD, Lin F, Hossain MA, Dawson RM (2012) Chemical synthesis and biological evaluation of an antimicrobial peptide gonococcal inhibitor. Amino Acids 43:2279-2283
42. Winterton N (2001) Twelve more green chemistry principles. Green Chem 3:G73-G75
43. Yu HM, Chen ST, Wang JT (1992) Enhanced coupling efficiency in solid-phase peptide synthesis by microwave irradiation. J Org Chem 57:4781-4784