Synthesis of 3-(12-hydroxy-p-carboranyl)propionic acid, a hydrophobic, N-terminal tyrosine-mimetic for peptides.
A new, p-carborane containing analog of tyrosine, namely 3-[1-hydroxy-1,12-dicarba-closo-dodecaboran(12)-12-yl]propionic acid was prepared from p-carborane in five steps involving hydroxypropylation of O-protected 1-hydroxy-p-carborane as the key transformation. The simple tyrosine mimetic can function as a hydrophobic surrogate for an N-terminal tyrosine residue in insect and mammalian neuropeptides to enhance the lipophilicity, and therefore, the cuticle and/or tissue permeability properties of mimetic analogs.
Ujváry
I
I
USDA-ARS, Southern Plains Agricultural Research Center, 2881 F & B Road, College Station, TX 77845, USA. istvan@cric.chermes.hu
Nachman
R J
RJ
D000818:Animals; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D019476:Insect Proteins / Q000737:chemistry; D009479:Neuropeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry*; D014443:Tyrosine
D001896:Boron Compounds; D019476:Insect Proteins; D009479:Neuropeptides; D011422:Propionates; D014443:Tyrosine