期刊
PEPTIDES
卷 23, 期 4, 页码 795-799出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/S0196-9781(01)00650-7
关键词
p-carboranes; insect peptides; synthesis; tyrosine analog
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. (C) 2002 Published by Elsevier Science Inc.
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