<P><B>Abstract</B></P><P>A new glycosyltransferase (UGT71E5) from <I>Carthamus tinctorius</I> exhibited a robust promiscuity towards 30 structurally diverse drug‐like aromatic amine scaffolds, making it the first reported glycosyltransferase capable of catalyzing <I>N</I>‐glycosylation with multiple diverse nitrogen‐heterocyclic aromatic compounds. The catalytic promiscuity and reversibility of UGT71E5 was exploited to generate the rare <I>N</I>‐glycoside from the abundant <I>O</I>‐glycoside with high efficiency. These findings demonstrate the significant potential of UGT71E5 in the enzymatic synthesis of diverse bioactive <I>N</I>‐glycosides.</P>