Synthesis of dityrosine cross-linked peptide dimers using the Miyaura-Suzuki reaction

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2817-2820

  Yoburn, Joshua C ^a   Van Vranken, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; DIMER; PALLADIUM; PEPTIDE; PEROXIDASE; PHENOL DERIVATIVE; POTASSIUM CARBONATE; TYROSINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS LINKING; MIYAURA SUZUKI REACTION; MOLECULAR INTERACTION; SYNTHESIS;

DIMERIZATION; PEPTIDES; TYROSINE;

EID: 0141451979     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034801t     Document Type: Article

References (18)

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16. ESI-MS of the transient TLC spot is consistent with an aryl boronate intermediate. Ironically, the aryl iodide (m/z 453.04) and the aryl boronate (m/z 453.23) have similar m/z and were therefore difficult to distinguish by low-resolution mass spectrometry.
17. 2dppf (10 mol %), and bispinacolatodiboron (60 mol %). The solids were flushed with nitrogen for 5 min prior to the addition of DMSO. The reaction was heated to 90°C for 6-72 h. Concentration in vacuo followed by silica gel chromatography provided the dityrosine cross-linked peptide dimer.
18. 2dppf (20 mol %), and bispinacolatodiboron (20 mol %) and sufficient DMSO to solubilize the reagents (about 0.125 M). The reaction was again heated at 90°C for 3-6 h. Concentration in vacuo followed by silica gel chromatography provided the dityrosine cross-linked peptide dimer.