Can anyone offer guidance on the best pattern to address the use of apostrophes in email addresses?

I have email addresses such as O'Conner@, O'Brian@, O'Dwyer@, d'Obrain@ etc

The EnterpriseManager and User eSpaces and do not send emails to these addresses despite the fact that apostrophes are permitted local part of the address, before the @ symbol in an email address in the RFC 5322.

This causes a problem when the platform is asked to send password reminders and other system generated emails.

It appears in eSpaces where I create the email, emails are formed and sent without error.

What happens if you encode the apostrophe?  Can you change from ' to %27 and then send?

using '%27' is sadly bounced by the receiving email server as #550 5.1.1 RESOLVER.ADR.RecipNotFound;

Could you escape it? O\'Conner@

Sorry for the guesses... I don't usually do the "try this" thing in posts... but I don't have a project with email to test with.