The letter kuf (which should not be confused with the letter kaf) represents the concept of holiness because it is the first letter of the word k’dusha (as well as: kiddush, kaddish, kadosh, all of which represent sanctification/holiness). To be holy, or to sanctify something and make it holy, is, in actuality, the act of separating that object from the mundane and elevating it to a state of holiness. A silver goblet holds no special meaning until one fills it with wine and blesses that wine in order to honor the Sabbath. Perhaps this is why the form of the letter kuf is separated into two pieces.
The numerical value of kuf is 100, which represents completion, an entire unit. This concept of completion is also symbolic of God’s holiness.
The name of the letter, kuf, is closely related to the word monkey (kof). At a quick glance, when looking at the shape of the kuf, one can actually see the physical shape of a monkey crouched down with its tail hanging.
Kuf, however, also derives from the same root of the word hakif, which means to go around. Kuf, therefore, is representative of the cycle of the seasons and the year, as well as having a connection to the hakafot (circuits of dancing with the Torah) on Simchat Torah.
Bibliographical acknowledgment: The Wisdom In The Hebrew Alphabet: The Sacred Letters as a Guide to Jewish Deed and Thought. By Rabbi Michael L. Munk. Mesorah Publications, 1983.