| Title: | Synthesis of peptides containing C-terminal methyl esters using trityl side-chain anchoring: application to the synthesis of a-factor and a-factor analogs |
| Author(s): | Diaz-Rodriguez V; Mullen DG; Ganusova E; Becker JM; Distefano MD; |
| Address: | "Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA" |
| ISSN/ISBN: | 1523-7052 (Electronic) 1523-7060 (Print) 1523-7052 (Linking) |
| Abstract: | A new cysteine anchoring method was developed for the synthesis of peptides containing C-terminal cysteine methyl esters. This method consists of attachment of Fmoc-Cys-OCH(3) to either 2-ClTrt-Cl or Trt-Cl resins (via the side-chain thiol) followed by preparation of the desired peptide using Fmoc-based SPPS. We applied this method to the synthesis of the mating pheromone a-factor and a 5-FAM labeled a-factor analog. The peptides were obtained with high yield and purity and were shown to be bioactive in a growth arrest assay |
| Keywords: | Amino Acid Sequence Cysteine/*chemistry Esters Molecular Structure Peptides/*chemical synthesis/chemistry Sex Attractants/*chemical synthesis/chemistry; |
| Notes: | "MedlineDiaz-Rodriguez, Veronica Mullen, Daniel G Ganusova, Elena Becker, Jeffrey M Distefano, Mark D eng T32 GM008700/GM/NIGMS NIH HHS/ GM008700/GM/NIGMS NIH HHS/ GM058842/GM/NIGMS NIH HHS/ R01 GM081388/GM/NIGMS NIH HHS/ GM084152/GM/NIGMS NIH HHS/ R01 GM084152/GM/NIGMS NIH HHS/ GM22087/GM/NIGMS NIH HHS/ R56 GM022087/GM/NIGMS NIH HHS/ R01 GM058842/GM/NIGMS NIH HHS/ R01 GM022087/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural 2012/11/06 Org Lett. 2012 Nov 16; 14(22):5648-51. doi: 10.1021/ol302592v. Epub 2012 Nov 2" |
