Science of Synthesis

Nguyen, B. N.; Hii, K. K.; Szymański, W.; Janssen, D. B., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 643.

Ammonia lyases are enzymes that catalyze the reversible addition of ammonia to double bonds. To date, over 20 such enzymes have been characterized and their properties have been reviewed.[‌171‌] Different mechanisms of action can be found within this family of enzymes, which require different internal or external cofactors, such as 4-methyleneimidazol-5-one (MIO), pyridoxal phosphate, coenzyme B12, or chelated metals. This review will focus on ammonia lyases and mutases for which synthetic utility has been reported.

Mee eeeeee eeee MMM-eeeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeee eeeeeeeeeee ee eeeeeee eeee α-eeeee eeeee.[‌888‌] Mee eeeeeeeee ee eeee eeeeeeeeeeeeee eeeeee ee eee eeeeeeeeee eeeee MMM, eeeee ee eeeeee eeeeeeeeeeeeeeeee ee eee eeeeee eeee eeee eee eeeeeeee eeeeeeeeee Mee-Mee-Mee. Me eee eeeeeeeeee eeeeeeee eeee e Meeeeee–Meeeee-eeee eeeeeeee eeeeee eeeeeee MMM eee eee eeeeeeee eeee ee eee eeeeeeeee, eeee eeeeeeeeee eeeeeeeeeee ee eeeeeee ee eeeee eee α,β-eeeeeeeeeee eeeeeeeeee eeee. Me eee eeeeeee eeeeeeeee, MMM eeee ee ee eeeeeeeeeeee eeee eeeeee eeee eee α-eeeee eeee eeeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeeeeeeee ee ee eeeee eeee eeee eeeeeeeeeeee eeeeeeee eeee eee eeeeeeeee ee e MMM–eeeeeee eeeeee eeee eee eeeeee eeeeeee eeeeeeeeeee ee eeeeeee eeeeeee (eeeee eeeee), ee eee ee e eeeeeeeeeee eeee eeeeeee eee α,β-eeeeeeeeeee eeeeeeeeee eeee (eeeeee eeeee).

‌Meeeee 88‌ Meeeeeee Meeeeeeeee eee MMM-Meeeeeeeee Meeeeee[‌888‌]

Meee eeee eeeee ee eeeeeee, eeeeeeeeeeeee eeeeeee eeeee (MMM) eee eee eeeeeee eeeeeee eeeeeeeeeeeee eeeeeeeeeee (MMM) eee ee eeeeeee eeeeeeeee eeeeeeee, ee eeee eeee eeee eeeeeeee ee eeeeeeee eee eeeeeeee ee eeeeeee ee α,β-eeeeeeeeeee eeeeeeeeee eeeee ee eeee eeeeeeeeeeeeee ee eeeeeee (>8 M).

Meeeeeeeeeeee eeeeeee eeeee (MM 8.8.8.8) eeeeeeeee eee eeeeeeeeee eeeeeeee ee eeeeeee ee eeeeeeee eeee eee eee eeeeeeeee eeee eeeeeee eeeeeeeeeeeeeeeeee, eeeeeeeeee eee eeeeeee eeee >88% ee ee eee (M)-eeeeee (‌Meeee 88‌).[‌888‌–‌888‌] Me eeee eeee eeeeeeeeeeeeee ee eeeeeee (ee eee eeee) ee ee eeeeeeee ee eeeeeeee eee eeeeeeeeeee eeeeeeeeeee ee eee eeeeeeee. Mee eeeeeeeeeee eee ee eeee eeee ee eee eeeeeeee eeeeee eee ee e eeeee-eeee eeeeeeeeeee.

‌Meeee 88‌ Meeeeeeeeeeee Meeeeee Meeee Meeeeeeee Meeeeeee ee Meeeeee ee Meeeeeee Meeee[‌888‌–‌888‌]

e Meeeeeeeee ee eeeeeeeeee ee eee eeeeeeeeeeeee ee e-eeeeeeeeeeeee eeeee ee eeeee eeee eeeeeeee.

e Meeeeeeeee ee eeeeeeeeee ee MMMM.

Me eeeeeeeeee, eee eeeeeeeeeeeee eeeeeeeee eeeee eeeeeeeeeeeee eeeeeeeeeee (MMM) eee eeee eeeeeeeeeeeeee, eeeeeee ee eee eeeeeeeee ee e eeeeeee ee α- eee β-eeeeeeeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee Meeeeeeeeee Meeeeeeee Meeeeeee ee Meeeeee ee Meeeeeee Meee Meeeeeeee[‌888‌]

Meeeeee eeeeeee eeeeeeee eeee β-eeeee eeeee eee eeeeeee eee eeeeeeee eeeee eeeeeeeeeee eeee eeeeeeee-eeeeeeee eeeeee (eeeee, eeeeee), eeeee eee α-eeeeeee eee eeeeeeeeeeeee eeeeeeee eeee eeeeeeee eeeee eeee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee.[‌888‌,‌888‌] Mee eeeeeeee eeee eeeeeeeeeeeee eeeeeeee eeee eeeeee ee eeeeeeeeeeeee 8:8 eeeeeee ee eeeeeeeeeee eeeeeeee (‌Meeeee 88‌). M eeeeeeeeee eeeeee eee eee eeeeeeeeee ee eeeee eeeeeee ee eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeee Meeeeeeeeee Meeeeeeee Meeeeeee ee Meeeeee ee Meeeeeee Meee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeee-8-eeeeeeeeeeeeeee Meee (‌88‌, Me8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeee MM8 eeee (88 eM) eee eeeeeee eeee M8M (88 eM) eee eee eM eee eeeeeeee ee 88 ee eeeeeeee MM8 eeeeeee eee eeee. (M)-Meeeeeee eeee (888 ee, 8.888 eeee) eee eeeeeeeeeee ee-MMM (Meeeeeeeeeee eeeeeee) (8 eeee) eeee eeeee ee eeee eeee eee eee eeeeeee eee eeeeeeee eeeeeeeee ee 88 °M. Mee eeee eee eeeeeeeee eeee 8% MMe (ee eM 8.8), eeeeee ee eeeeeee, eeeeeeee, eee eeeeeee ee e Meeee 88 eeeeee-eeeeeeee eeeeee. Mee eeeeeee eee eeee eee MM8 eeee, ee eeeeee eee eeeeeee; eeeee: 88 ee (88%).

8-Meeee-8-eeeeeeeeeeeeeee Meee (‌88‌) eee 8-Meeee-8-eeeeeeeeeeeeeee Meee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

M 8 M ee MM8 eeee eee eeeeeeee eee eee eM eee eeeeeeee ee 88 ee eeeeeee MM8 eeeeeee eee eeee. (M)-Meeeeeee eeee (88 ee, 8.8 eeee) eee eeeee, eeeeeeee ee MMM (8.8 ee), eee eee eeeeeee eee eeee ee ee. Meeee 88 e, eeeeeee eeeeeee ee eee eeeeee (8.8 ee) eee eeeee. Meeee 8 e, eee eeeeeee eee eeeeeeeeeee, eeeeeeeeeee ee 8 M ee MMe (88 eM), eee eeeeee ee e eeeeee eeeeee eeee eee-eeeeeeee eeeee (Meeee 88). Mee eeeeee eee eeeeee eeee M8M eee eee eeeeeee eee eeeeee eeee 8 M ee MM8MM. Meeeeeeee-eeeeeeee eeeeeeeee eeee eeeeeeeee eee eeeeeeeeeee ee eeeee ee eeeeeeeeeeeee 8:8 eeeeeee ee α- eee β-eeeeeeeeeeeeee; eeeee: 88 ee (88%).

References