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Amino acids surrogates: an indirect method for the synthesis of peptides containing the thioasparaginyl residue

✍ Scribed by Hossain Saneii; Arno F. Spatola

Book ID: 104220271
Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 247 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)86771-4

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✦ Synopsis

The protected pentapeptide, Boc-Tan-Cys(PMB)-Pro-Leu-GlyNH2+ and related thioasparaginyl compounds were prepared by an indirect method from their corresponding B-cyanoalanyl precursors by treatment with H2S/NH3. The optical purities of thioasparagine (Tan) derivatives were evaluated by two different approaches. Previously three separate groups have successfully synthesized peptide derivatives containing the thioamide function in the backbone, du Vigneaud,l Lawesson,2 and Ried.3 The synthesis of various protected derivatives of thioasparagine (H2NCH(CH2CSNH2)C02H) was first reported by Ressler and Banerjee.4 However, from our own work in this area, it appeared unlikely that thioasparagine-

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