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Synthesis of (S)-3-(1-hydroxy-p-carboran-12-yl)alanine, a novel hydrophobic tyrosine-mimetic for peptides.
Ujváry, István; Nachman, Ronald J.
Afiliação
  • Ujváry I; USDA -ARS, Veterinary Entomology Research Laboratory, Southern Plains Agricultural Research Center, 2881 F & B Road, College Station, TX 77845, USA.
Peptides ; 23(4): 795-9, 2002 Apr.
Article em En | MEDLINE | ID: mdl-11897400
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.
Assuntos
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Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Tirosina / Neuropeptídeos / Compostos de Boro / Alanina Limite: Animals Idioma: En Revista: Peptides Ano de publicação: 2002 Tipo de documento: Article País de afiliação: Estados Unidos País de publicação: Estados Unidos
Buscar no Google
Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Tirosina / Neuropeptídeos / Compostos de Boro / Alanina Limite: Animals Idioma: En Revista: Peptides Ano de publicação: 2002 Tipo de documento: Article País de afiliação: Estados Unidos País de publicação: Estados Unidos