The growth-inhibitory effect of 23 carbohydrate monoesters synthesized by lipases and proteases were assayed to obtain antibacterial agents that suppress the cell growth of Streptococcus mutans. Among the carbohydrate esters synthesized, galactose and fructose laurates showed the highest growth-inhibitory effect, while the other analogs of hexose laurates showed no antibacterial activity, indicating that configuration of the hydroxyl group in carbohydrate moiety markedly affects the antibacterial activity. The cell growth of S. mutans was suppressed by fructose laurates even in the presence of sucrose. Thus, enzymatic synthesis of carbohydrate esters with different core structures has great potential for developing antibacterial agents applicable to food additives.