Synthesis of DNA-Carbohydrate Conjugate via Diazocoupling: A New Class of Modified DNA with Enhanced Stability and Lectin-Recognition Ability

Salmon testes DNA was treated with a diazonium salt connected to N-(beta)-lactoside via a spacer chain to yield a diazo coupling product with a degree of substitution of 0.14. The DNA-lactose conjugate kept a typical B-type conformation similar to native DNA, and showed higher melting temperature and stronger nuclease resistance than native DNA. The conjugate was found to acquire a strong binding affinity to galactose-specific lectin RCA120.