2-N-Acetylglucosamine-α-O-threonine, an amino acid derivative from the marine sponge Cinachyrella kuekenthali

• Willian Henríquez Universidad de Oriente-Venezuela
• Carlos Sevcik Universidad de Oriente-Venezuela
• Gina D”™Suze Universidad de Oriente-Venezuela
• Gonzalo Visbal Instituto Venezolano de Investigaciones Científicas (IVIC)-Venezuela
• Carsten Christophersen University of Copenhagen-Dinamarca

Palabras clave: cinachyrella kuekenthali, Amino acid, 2-N-acetylglucosamine- α -O-threonine

Resumen

A new amino acid derivative, 2-N-acetylglucosamine- α -O-threonine [2-N-AcNGlc- α -O-Thr, (1)], was isolated from the marine sponge Cinachyrella kuekenthali. The structure assignment is based on interpretation of NMR spectroscopic data. The orientation of the α -O-glucosamine bond was deduced from the value of the (J = 3.7 Hz) coupling constant of the anomeric proton and the position of the 2-N-acetylglucosamine moiety on the value of the (α C 56.2) carbon chemical shift of the C2-position. The amino acid derivative was inactive on the Sk Br-3 (breast) and HT-29 (colon) human cancer cell lines and MA-104 kidney monkey cell line.