Recently, syrups of various homo- and hetero-oligosaccharides are on the market for the food in-dustry. Production and application of some oligosaccharides are reviewed in this report. (1) Coupling sugar: The syrup which contains glucosyl-sucrose, maltosyl-sucrose, etc. as the main compo-nent was produced by using the action of a transfer enzyme. The syrup inhibited the synthsis of in-soluble glucan from sucrose using Streptococcus mutans. This finding proved the syrup is a sweetener which hardly induces dental caries. (2) Fructooligosaccharides: This syrup contains fructofuranosylsucrose oligomers. The administration of these oligosaccharides has been reported to be effective in stimulating the growth of bifidobacteria in the human intestinal canal. (3) A novel enzymatic production system of trehalose was developed. Industrial production of trehalose has become possible using this system. (4) Branched cyclodextrins containing heterogeneous sugars and larger cyclodextrins (cycloamylose), which have more than 17 glucose units in the ring, have been prepared by some transfer enzymes. (5) For the increase of bioavailability of dietary calcium, phosphoryl oligosaccharides from potato starch have been studied.