Use of the 2-Chlorotrityl Chloride Resin for Microwave-Assisted Solid Phase Peptide Synthesis

被引:24
|
作者
Ieronymaki, Matthaia [1 ]
Androutsou, Maria Eleni [1 ,2 ]
Pantelia, Anna [1 ]
Friligou, Irene [1 ,2 ]
Crisp, Molly [3 ]
High, Kirsty [3 ]
Penkman, Kirsty [3 ]
Gatos, Dimitrios [1 ]
Tselios, Theodore [1 ]
机构
[1] Univ Patras, Dept Chem, Rion 26504, Greece
[2] Eldrug SA Pharmaceut Co, Platani 26504, Greece
[3] Univ York, Dept Chem, BioArCh, York YO10 5DD, N Yorkshire, England
关键词
solid phase peptide synthesis; microwave assisted peptide synthesis; 2-chlorotrityl chloride resin; racemization; MYELIN OLIGODENDROCYTE GLYCOPROTEIN; EXPERIMENTAL AUTOIMMUNE ENCEPHALOMYELITIS; EXPERIMENTAL ALLERGIC ENCEPHALOMYELITIS; SCLEROSIS-LIKE DISEASE; MULTIPLE-SCLEROSIS; BASIC-PROTEIN; IMMUNODOMINANT EPITOPE; AMINO-ACIDS; INDUCTION; LIGANDS;
D O I
10.1002/bip.22710
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A fast and efficient microwave (MW)-assisted solid-phase peptide synthesis protocol using the 2-chlorotrityl chloride resin and the Fmoc/tBu methodology, has been developed. The established protocol combines the advantages of MW irradiation and the acid labile 2-chlorotrityl chloride resin. The effect of temperature during the MW irradiation, the degree of resin substitution during the coupling of the first amino acids and the rate of racemization for each amino acid were evaluated. The suggested solid phase methodology is applicable for orthogonal peptide synthesis and for the synthesis of cyclic peptides. (C) 2015 Wiley Periodicals, Inc.
引用
收藏
页码:506 / 514
页数:9
相关论文
共 50 条
  • [21] Microwave-assisted Solid Phase Peptide Synthesis on High Loaded Resins
    Stéphanie Coantic
    Gilles Subra
    Jean Martinez
    International Journal of Peptide Research and Therapeutics, 2008, 14 : 143 - 147
  • [22] The effect of peptide length on the cleavage kinetics of 2-chlorotrityl resin-bound ethers
    Kocsis, Laszlo
    Ruff, Ferenc
    Orosz, Gyorgy
    JOURNAL OF PEPTIDE SCIENCE, 2006, 12 (06) : 428 - 436
  • [23] RACEMIZATION-FREE SYNTHESIS OF C-TERMINAL CYSTEINE-PEPTIDE USING 2-CHLOROTRITYL RESIN
    FUJIWARA, Y
    AKAJI, K
    KISO, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (03) : 724 - 726
  • [24] Solid-Phase Peptide Synthesis in Water Using Microwave-Assisted Heating
    Galanis, Athanassios S.
    Albericio, Fernando
    Grotli, Morten
    ORGANIC LETTERS, 2009, 11 (20) : 4488 - 4491
  • [25] Microwave-Assisted Solid Phase Synthesis of Different Peptide Bonds: Recent Advancements
    Mukhia, Munna
    Pradhan, Kiran
    Biswas, Kinkar
    CURRENT MICROWAVE CHEMISTRY, 2023, 10 (02) : 155 - 179
  • [26] Microwave-assisted guanidinylation in solid phase peptide synthesis: comparison of various reagents
    Witkowska, Ewa
    Kubik, Karolina
    Krosnicka, Jolanta
    Grabowska, Karolina
    Niescioruk, Anna
    Wilenska, Beata
    Misicka, Aleksandra
    TETRAHEDRON LETTERS, 2014, 55 (45) : 6198 - 6203
  • [27] Advances in automatic, manual and microwave-assisted solid-phase peptide synthesis
    Sabatino, Giuseppina
    Papini, Anna M.
    CURRENT OPINION IN DRUG DISCOVERY & DEVELOPMENT, 2008, 11 (06) : 762 - 770
  • [28] MICROWAVE-ASSISTED GUANIDINYLATION IN SOLID PHASE PEPTIDE SYNTHESIS: COMPARISON OF VARIOUS REAGENTS
    Witkowska, E.
    Kubik, K.
    Krosnicka, J.
    Grabowska, K.
    Niescioruk, A.
    Wilenska, B.
    Misicka, A.
    JOURNAL OF PEPTIDE SCIENCE, 2014, 20 : S149 - S149
  • [29] Efficient solid-phase synthesis of sulfated tyrosine-containing peptides using 2-chlorotrityl resin: Facile synthesis of gastrin/cholecystokinin peptides
    Kitagawa, K
    Aida, C
    Fujiwara, H
    Yagami, T
    Futaki, S
    TETRAHEDRON LETTERS, 1997, 38 (04) : 599 - 602
  • [30] Microwave-assisted solid-phase synthesis of 2,5-diketopiperazines: Solvent and resin dependence
    Tullberg, Marcus
    Luthman, Kristina
    Grotli, Morten
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2006, 8 (06): : 915 - 922