Solid phase synthesis of mono- or disubstituted arginine containing peptides from an isothiocitrulline precursor

Tetrahedron Letters

Volumn 46, Issue 43, 2005, Pages 7349-7353

  Hamzé, Abdallah ^a   Gandreuil, Céline ^a   Lisowski, Vincent ^a   Andureu, Florence ^a   Fulcrand, Pierre ^a   Martinez, Jean ^a   Hernandez, Jean François ^a  

^a CNRS   (France)

Author keywords

Arginine; Fmoc NCS; Guanidine; Solid phase synthesis; Thiocitrulline

Indexed keywords

AMINE; ARGININE DERIVATIVE; CITRULLINE; LYSINE; ORNITHINE;

ARTICLE; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; SOLID STATE; SUBSTITUTION REACTION;

EID: 25444443659     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.120     Document Type: Article

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33. 6): δ 8.28 (m, 1H), 7.98-7.90 (m, 4H), 7.83 (d, J = 7.9 Hz, 1H), 7.19 (s, 1H), 7.05 (s, 1H), 4.28 (m, 1H), 4.16 (m, 1H), 4.02 (m, 1H), 3.70 (m, 2H), 3.58-2.95 (m, 10H), 2.83 (s, 3H), 2.05-1.14 (m, 8H+3H), 0.93-0.62 (m, 12H).
34. 39.
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37. Purity of the peptides was assessed by reverse-phase HPLC analysis using two sets of conditions.
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39. 3CN. Gradient, 5-60% B in A in 30 min. Flow rate, 1 mL/min.
40. For instance, use of diisopropylamine produced the expected compound in low yield (17% after purification).