title: Aqueous microwave-assisted solid-phase peptide synthesis using fmoc strategy. II. Racemization studies and water based synthesis of cysteine-containing peptides.
abstract: We have developed a microwave (MW)-assisted peptide synthesis using Fmoc-amino acid nanoparticles in water previously. It is an organic solvent-free, environmentally friendly method for peptide synthesis. In this study, we have investigated the racemization of cysteine during an aqueous based coupling reaction with MW irradiation. Under our MW-assisted protocol using WSCI and DMTMM, the coupling reaction can be performed with low levels of racemization of cysteine. We also demonstrated the synthesis of the nonapeptide oxytocin analogue, Cys(Acm)-Tyr-Ile-Gln-Asn- Cys(Acm)-Pro-Leu-Gly-NH2 using our water based MW-assisted protocol with Fmoc-amino acid nanoparticles.
authors.affiliation: Faculty of Pharmaceutical Sciences & Cooperative Research Center of Life Sciences, Kobe Gakuin University, 1-1-3 Minatojima, Chuo-ku, Kobe 650-8586, Japan. hojo@pharm.kobegakuin.ac.jp
authors.forename: Keiko
authors.initials: K
authors.lastname: Hojo
authors.forename: Natsuki
authors.initials: N
authors.lastname: Shinozaki
authors.forename: Asaki
authors.initials: A
authors.lastname: Hara
authors.forename: Mare
authors.initials: M
authors.lastname: Onishi
authors.forename: Yoshinobu
authors.initials: Y
authors.lastname: Fukumori
authors.forename: Hideki
authors.initials: H
authors.lastname: Ichikawa
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D003545:Cysteine / Q000138:chemical synthesis / Q000737:chemistry*; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D053758:Nanoparticles / Q000737:chemistry*; D010121:Oxytocin / Q000031:analogs & derivatives*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D014867:Water / Q000737:chemistry
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D014867:Water; D010121:Oxytocin; D003545:Cysteine