Deutsche Bank AG will pay a $258 million penalty to settle charges that it did business on behalf of entities in U.S.-sanctioned countries like Iran and Syria, the New York Department of Financial Services (NYDFS) and Federal Reserve said on Wednesday.

Germany's largest bank conducted $10.9 billion in clearing transactions for the customers from 1999 to 2006, using "non-transparent methods and practices" to shield them from scrutiny, the New York State regulator said.

The settlement requires Deutsche Bank to hire an independent monitor and fire six employees. It will pay $200 million of the penalty to NYDFS and the remaining $58 million to the Fed.

"The conduct ceased several years ago, and since then we have terminated all business with parties from the countries involved," a Deutsche Bank spokeswoman said in a statement.