O-acyl isopeptide method: efficient synthesis of isopeptide segment and application to racemization-free segment condensation.
We report the establishment of the O-acyl isopeptide method-based racemization-free segment condensation reaction toward future chemical protein synthesis. Peptide segments containing C-terminal O-acyl Ser/Thr residues were successfully synthesized by use of a lower nucleophilic base cocktail for Fmoc removal, and then coupled to an amino group of a peptide-resin without side reactions or epimerization. We also succeeded in performing the segment condensation in a sequential manner and in solution phase conditions as well.
Yoshiya
Taku
T
Department of Medicinal Chemistry, Division of Medicinal Chemical Sciences, Center for Frontier Research in Medicinal Science, 21st Century COE program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, 607-8412, Japan.
Kawashima
Hiroyuki
H
Sohma
Youhei
Y
Kimura
Tooru
T
Kiso
Yoshiaki
Y
D000588:Amines / Q000737:chemistry; D000595:Amino Acid Sequence; D047908:Intracellular Signaling Peptides and Proteins / Q000138:chemical synthesis / Q000737:chemistry; D008969:Molecular Sequence Data; D009479:Neuropeptides / Q000138:chemical synthesis / Q000737:chemistry; D000068797:Orexins; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014520:Urethane / Q000737:chemistry; D014763:Viral Matrix Proteins / Q000138:chemical synthesis / Q000737:chemistry
D000588:Amines; D047908:Intracellular Signaling Peptides and Proteins; D009479:Neuropeptides; D000068797:Orexins; D010446:Peptide Fragments; D010455:Peptides; D014763:Viral Matrix Proteins; C427211:humanin; C448634:influenza matrix peptide (58-66); D014520:Urethane