Departamento de Química, Universidad de La Rioja , Centro de Investigación en Síntesis Química, E-26006 Logroño, Spain.
J Am Chem Soc. 2014 Jan 15;136(2):789-800. doi: 10.1021/ja411522f. Epub 2014 Jan 7.
Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(β-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.
立体选择性的硫代-Michael 加成反应，即将适当保护的硫代碳水化合物与手性脱氢丙氨酸加成，是合成具有重要生物学意义的半胱氨酸衍生物的关键步骤，如 S-(β-D-吡喃葡萄糖基)-D-半胱氨酸，目前尚未合成，以及 S-(2-乙酰氨基-2-脱氧-α-D-半乳糖吡喃基)-L-半胱氨酸，可被视为 Tn 抗原的类似物。还从构象角度合成和分析了相应的二酰胺衍生物，并研究了其与凝集素的结合状态。
