Synthesis of (S)-3-(1-hydroxy-p-carboran-12-yl)alanine, a novel hydrophobic tyrosine-mimetic for peptides.

Abstract:

: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.

journal_name

Peptides

journal_title

Peptides

authors

Ujváry I,Nachman RJ

doi

10.1016/s0196-9781(01)00650-7

subject

Has Abstract

pub_date

2002-04-01 00:00:00

pages

795-9

issue

4

eissn

0196-9781

issn

1873-5169

pii

S0196978101006507

journal_volume

23

pub_type

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