Synthesis of (S)-3-(1-hydroxy-p-carboran-12-yl)alanine, a novel hydrophobic tyrosine-mimetic for peptides.
A new, p -carborane containing analog of tyrosine, 3-[1-hydroxy-1,12-dicarba-closo-dodecaboran (12)-12-yl]alanine, was prepared from protected 3-[1-hydroxy-1,12-dicarba-closo-dodecaboran (12)-12-yl]propionic acid in five steps using Oppolzer's sultam methodology for asymmetric hydroxyamination as the key step. The tyrosine mimetic can function as a hydrophobic surrogate for tyrosine residues in insect and mammalian neuropeptides to enhance the lipophilicity, and therefore, the cuticle and/or tissue permeability properties of mimetic analogs. As an amino acid, insertion of the mimic is not limited to the N-terminus but can replace a tyrosine residue at any position within a peptide sequence.
Ujváry
István
I
USDA -ARS, Veterinary Entomology Research Laboratory, Southern Plains Agricultural Research Center, 2881 F & B Road, College Station, TX 77845, USA.
Nachman
Ronald J
RJ
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D019476:Insect Proteins / Q000737:chemistry; D007313:Insecta / Q000737:chemistry; D015394:Molecular Structure; D009479:Neuropeptides / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry*
C467327:3-(1-hydroxy-4-carboran-12-yl)alanine; D001896:Boron Compounds; D019476:Insect Proteins; D009479:Neuropeptides; D014443:Tyrosine; D000409:Alanine