N→S acyl-transfer-mediated synthesis of peptide thioesters using anilide derivatives

Organic Letters

Volumn 11, Issue 4, 2009, Pages 823-826

  Tsuda, Shugo ^a   Shigenaga, Akira ^a   Bando, Kiyomi ^a   Otaka, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; ESTER; NITROGEN; PEPTIDE; SULFUR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANILIDES; ESTERS; MOLECULAR STRUCTURE; NITROGEN; PEPTIDES; SULFUR;

EID: 62749199817     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8028093     Document Type: Article

References (44)

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31. After coupling of Boc-Leu-OH to L-or D-Ala derivative, no epimerization was detected, which indicates that coupling of Fmoc-Ala-Cl with the sodium amide resulting from 12 and NaH does not induce an observable level of racemization. This coupling protocol can be used for other amino acids (Phe, Leu, Val, Ile), although application of the resulting coupling products to the N→S acyl transfer is underway.
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34. Little N→S acyl transfer occurred during short TFA treatment (at room temperature for ca. 30-90 min) for removal of side-chain protecting groups.
35. Neither decomposition of the anilide linkage nor epimerization at the Ala residue was observed by HPLC analyses of reactions of 14 with 20% piperidine/DMF; see the Supporting Information.
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38. Compared to HCl/dioxane, HC1/DMF shows a powerful solubilizing performance for deprotected peptides.
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42. N→S acyl transfer with HC1/DMF proceeds at about two times the reaction rate compared with that with TFA; see the Supporting Information.
43. Treatment of HPLC-purified thioester sample
44. (Phe-Ala-L-Alathioester) with 4 M HCl/DMF at 37 °C for 4 h afforded a mixture of diastereomers (parent peptide (80%) and epimerized Phe-Ala-D-Ala-thioester (20%)).