Studies on amino acids and peptides VIII : Synthesis and crystal structure of two monothiated analogues of Boc-Gly-S-Ala-Aib-OMe☆

Add time:09/24/2019    Source:sciencedirect.com

The model tripeptide Boc-Gly-S-Ala-Aib-OMe (2b) and the two monothiated analogues Boc-Gly(1ψ2CSNH)-S-Ala-Aib-OMe (2c) and Boc-Gly-S-Ala(2ψ3 CSNH)-Aib-OMe (2a) were synthesized. Peptide 2a was obtained by thiation of 1a using 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, Lawesson's Reagent (LR), followed by deprotection of the Boc group and coupling with Boc-Gly-OH. Thiation of 2b with LR regiospecifically transformed the protected tripeptide to the monothiated analogue 2c. X-Ray diffraction analysis showed that the type-III β-turn formed by the reference peptide 2b is preserved in the monothiated analogue 2a; conversely,the structure of the isomeric tripeptide 2c is partially extended.

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