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
Peptidesjournal_title
Peptidesauthors
Ujváry I,Nachman RJdoi
10.1016/s0196-9781(01)00650-7subject
Has Abstractpub_date
2002-04-01 00:00:00pages
795-9issue
4eissn
0196-9781issn
1873-5169pii
S0196978101006507journal_volume
23pub_type
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