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Hi.
You have to investigate if there are command line options to sign the documents.. If there are, then you can build an application that can read/select the documents and apply the command line options via call to (as an example) an Operating System script with the the appropriate arguments.
This is not an easy task given that the functionality you're mentioning has to invoke some sort of functionality outside of the database and ORDS. Of course you can build a service that listens for the right arguments and the service is the one that completes the request, a service of this kind is not in scope of Oracle APEX capabilities, it would need to be a Java, Shell, NodeJS kind of service... again, not an easy or beginner kind of task.
Good luck,
I'm agree with the above commentary.
I have seen that the best way is use "java" to create a sign routine, and call it using database.
However, remember that you have to store some sign files on the server, hence, this task is very difficult to use on the client side.