An efficient peptide ligation using azido-protected peptides via the thioester method

Tetrahedron Letters

Volumn 49, Issue 38, 2008, Pages 5492-5494

  Katayama, Hidekazu ^a   Hojo, Hironobu ^a   Ohira, Tsuyoshi ^b   Nakahara, Yoshiaki ^a  

^a TOKAI UNIVERSITY   (Japan)

^b KANAGAWA UNIVERSITY   (Japan)

Author keywords

Azido peptide; N Alkyl cysteine; Pigment dispersing hormones; Thioester method

Indexed keywords

AZIDE; COPPER; CYSTEINE; HORMONE DERIVATIVE; LYSINE; PEPTIDE DERIVATIVE; PIGMENT DISPERSING HORMONE; SILVER; THIOESTER; ZINC;

AMINO ACID SEQUENCE; ARTICLE; CROSS COUPLING REACTION; DEPROTECTION REACTION; NONHUMAN; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; POLYMERIZATION; SHRIMP;

EID: 48549100055     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.037     Document Type: Article

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18. Peptide segments 3a (450 μg, 0.50 μmol) and 4 (390 μg, 0.27 μmol) were dissolved in DMSO (50 μl) containing 10% 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine (HOObt) and 5% DIEA, and incubated at room temperature for 3 h. Piperidine (12.5 μl) was then added to this solution, and kept at room temperature for 20 min. The crude peptide was precipitated by the addition of 10 times volume of diethyl ether, washed twice with ether, and dried under vacuum. The precipitant was dissolved in 50% aq AcOH (300 μl) containing excess amount of Zn powder, and vortexed for 30 min. Zn powder was removed by filtration, and the desired product 6a was purified by RP-HPLC.
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