An automatic solid-phase synthesis of peptaibols.
An automated approach to peptaibols using microwave-assisted solid-phase peptide synthesis is demonstrated with a combination of HBTU and acid fluoride mediated couplings for normal and alpha,alpha-dialkylated amino acids, respectively. The method is utilized for the automated synthesis of several full-length peptaibols, including alamethicin, tylopeptin, ampullosporin, bergofungin, cervinin, trikoningin, trichogin, and peptaibolin, reducing both synthesis time and costs significantly as compared to other approaches. Furthermore, the use of noncommercially available reagents is minimized.
Hjørringgaard
Claudia U
CU
Center for Insoluble Protein Structures, Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Pedersen
Jan M
JM
Vosegaard
Thomas
T
Nielsen
Niels Chr
NC
Skrydstrup
Troels
T
D000408:Alamethicin / Q000138:chemical synthesis; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000737:chemistry; D008872:Microwaves; D008969:Molecular Sequence Data; D054848:Peptaibols; D010455:Peptides / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000138:chemical synthesis
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D054848:Peptaibols; D010455:Peptides; D010456:Peptides, Cyclic; C109004:ampullosporin; D000408:Alamethicin