A novel 2H-azirin-3-amine as a synthon for a sulfur-containing dipeptide segment

作者：Stoykova Svetlana A; Linden Anthony; Heimgartner Heinz^*

来源：Journal of Sulfur Chemistry, 2014, 35(1): 14-23.

DOI：10.1080/17415993.2013.774401

• 2H-azirin-3-amines
• N-(1-aza-6-thiaspiro[2
• 5]oct-1-en-2-yl)proline methyl ester
• -amino acids
• 4-aminotetrahydro-2H-thiopyran-4-carboxylic acid
• sulfur-heterocyclic amino acids

Starting with tetrahydro-2H-thiopyran-4-carboxylic acid and methyl prolinate, the novel 2H-azirin-3-amine [S]-N-(1-aza-6-thiaspiro[2.5]oct-1-en-2-yl)proline methyl ester was synthesized. In reactions with benzoic acid, thiobenzoic acid and Boc-valine, respectively, its usefulness as a synthon for the dipeptide [S]-N-[(4-aminotetrahydro-2H-thiopyran-4-yl)carbonyl]proline in peptide synthesis was demonstrated.

• 出版日期2014-1-2