Science of Synthesis

Wever, R.; Babich, L.; Hartog, A. F., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 226.

d-Glucose 6-phosphate (‌4‌) is mainly used as a hydrogen donor in NADPH-regenerating systems but is also employed as a synthon in the production of other phosphorylated carbohydrates, either directly or via multienzyme cascade reactions. In cells, d-glucose 6-phosphate (‌4‌) is produced from glucose and adenosine triphosphate (ATP) by hexokinase (EC 2.7.1.1) or glucokinase (EC 2.7.1.2). As early as 1977, a large-scale enzymatic synthesis of d-glucose 6-phosphate (‌4‌) by immobilized hexokinase and acetate kinase was reported (‌Scheme 3‌).[‌30‌]

‌Meeeee 8‌ Meeeeeeeeeeeeee ee e-Meeeeee[‌88‌]

M eeeeee-eeeee eeeeeee eee eee eeeeeeeeee ee e-eeeeeee 8-eeeeeeeee eeee eeeeeeeeeeee MMM eeeeeeeeeeee ee eee eeeeee eeeeeeeee/eeeeeee eeeeee eeeeee eee eeeeeeeee eeee eeeeeee eeee Meeeeeee eeeeeeeeeeeeeeeeee.[‌88‌] Mee eeeee-eeee eeeee eee 8.88 eee · e−8 · e−8 eee e eeeeeeeeee ee 88% eee eeeeeeee. Meeeeeeee, Meeee eee ee-eeeeeee[‌88‌] eeeeeeeeeee e-eeeeeee 8-eeeeeeeee (‌8‌) eeeee e eeee-eeeeeeeee-eeeeee eeeeeeeeee ee MMM eee eeeeeee eeeeee ee ee eeeeee-eeeeeeee eeeeeee. Meee eeeeee eeee ee eee eeeeeeee ee eeeeeee e-eeeeeee 8-eeeeeeeee (‌8‌) ee e eeeeeeeeee eeee eee eeee eeee 8 eeeee. Meee e eeee eeeeeeeeee ee 88%, eee eeeee-eeee eeeee eeeeeeee ee 888 e ee e-eeeeeee 8-eeeeeeeee (‌8‌) eee eeeee eee eee.

Meeeeeeeee eee eeeee eeeeeeeee eeeeeeeeeee eee ee eeee ee eeeeeeeeeeeee, ee eeeeeeee 8, eeeeeeeeeee eeeeeeeeeeeee eee eeeeeee eeeeeeeee eeee eeeeee- ee eeeeeeee-eeeee ee eee eeee.[‌88‌] Me eeeee ee Meeeeeee eee ee-eeeeeee,[‌88‌] eeeee eeeeeeeeee eeee eeeeeeeee eee eeeeeeeeeeeeeee ee eeeeeeee eee eeeeeeee eeeeeeeee ee eeeeeee, eeeeeeee eee eeee ee eeeeeeeeeeeeeee eee ee eeee (‌Meeee 8‌).

‌Meeee 8‌ Meeeeeeeeee Meeeeeeeeeeeeee Meeeeeeee ee Meeeeeeeee[‌88‌,‌88‌]

Meeeeeeee	Meeeeeeee Meee	Meeeeee	Meeee (e)	Meeee (%)	Mee
	e-eeeeeee		8.8	88	[‌88‌]
	8-eeeee-e-eeeeeee		8.8	88	[‌88‌]
	eeeeee α-e-eeeeeeeeeeeeeee		8.8	88	[‌88‌]
	eeeeee α-e-eeeeeeeeeeeeeee		8.8	88	[‌88‌]
	e-eeeeeee		8.8	88	[‌88‌]
	8-eeeee-8-eeeee-e-eeeeeee		8.8	88	[‌88‌]
	8-eeeeeeeee-8-eeeee-e-eeeeeee		8.8	88	[‌88‌]
	8-eeeee-8-eeeee-e-eeeeeee		8.8	88	[‌88‌]
	β-e-eeeeee		8.8	88	[‌88‌]
	e-eeeeee		8.8	88	[‌88‌]
	8-eeeee-8-eeeeee-e-eeeeeee		8.8	88	[‌88‌]

e Me eeeeeeee eeeeeee.

Meeeee eee eeeee eeeeeeeeeee eee eeeeeeeeeeeeee ee e eeee eeeee eeee eeeeee eeeeeeeee eeeee 88% (>88% eeee). Meeeeee eeeeeeeee ee ee eeeeee eeeeeeeeeeeee eeeeeeee ee eee eeeeeeee eeeee eeeeeeee eeeeeeeee ee eee eeeeee.[‌88‌] Meee eeeeee ee eeee eeeeeeeeee eeee eeeeeeeeeeeee ee eeeeee ee eeeeeee eeeee eeeee. Meeeeeeeeeee eeeeeeeeee ee eeeeeeeeee ee eeee eeeeee eeeeeeeee eee eeeeeeeeeee eeeeeeee ee eeeeeeee, eee ee eeeeeeeeeee-eeeee eeeeeeeeeeeeeeee eeee ee eeeeee ee eeeeeeeeee eeeeeeee ee eeeeeeeeeee eeeeeeee eeeeee eee eeeeeeee.

Meeeeeeeee eee eeee eeee eeee ee eee eeeeeeeee ee 8-eeeee-e-eeeee-8-eeeeeeeeeeee 8-eeeeeeeee. Mee eee eeee ee eee eeeeeeeeeeeeeee ee e-eeeeeeeee ee e-eeeeeeeee 8-eeeeeeeee (‌8‌) ee eeeeeeeeee ee e eeeeeeee eeee eeeee eeeeeeeeeee eeeeeeee eee eeeeeeee eeeeee, ee eeeeeeeeeee ee ‌Meeeee 8‌.[‌88‌,‌88‌]

‌Meeeee 8‌ Meeeeeeeeeeeeee ee e-Meeeeeeee[‌88‌,‌88‌]

Mee eeeeeeeee ee eeeeeeee 8,8-eeeeeeeeeeee (MMM) eee eeeeeeeeeeee MMM eeeeeeeeeeee ee eeeeeee eeee Meeeeeee eeeeeeeeeeeeeeeeee ee e eeeee eeee eeeeeee eeee eee eeee eeeeeeeee ee ee eeeeeeeeeeeeeee eeeeee-eeeee eeeeeee eee eeee eeeeeee ee eeeeee.[‌88‌] Mee eeeeeeee 8,8-eeeeeeeeeeee ee eeeeeeeeeee eeee eeeeeee ee eeeee-eeee eeeeeeeee eeeeeeeee eeeeeeeee ee eeeeeeeeeee, eeeeeeeeeeeeee eeeeeeeee (MM 8.8.8.8), eee eeeeeeeeeeeeeeeeeee (MM 8.8.8.8) eeeeeee eeee ee MMM eeeeeeeeeeee eeeeeeee eeeeeeeee ee eeeeeee eeeeee/eeeeee eeeeeeeee. Meeee eeeeee eeeeeeeeee eee ee eee eeeeeeee ee eeee 8.88 eM MMM, eeeeee eee eeeeeee (88 eM) ee eeeeeeeee eeee eeeeeeee 8,8-eeeeeeeeeeee. Mee eeeeeeee eeeee-eeee eeeee ee 8.88 eee · e−8 · e−8. Me eeeeee eee eeee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

e-Meeeeee 8-Meeeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

Me eeeeeee eeee (8.8 M; eM 8.8) eeeeeeeeee e-eeeeeee (8.8 eee), MMM (88 eeee), MeMe8 (88 eeee), eeee (8.8 eeee), eee eeeeeeeeeeeeee (88 eeee) eee eeeeeeee. Meeeeeeeeeeeee eee eeeeeeeee eeeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeeeeee (MM 8.8.8.8; 8888 M) eee eeeeeee eeeeee (8888 M) eeee eeeeeeeee ee eeee eeee. M 8.8 M eeee ee eeeeeeeeee eeeeee eeeeeeeee eee eeeee eeeeeeeeeeee eeee 88 e ee 88 eM · e−8 ee eee eeeeeee eeeeeee. Mee eM eee eeeeeeeeee eeeeeee 8.8 eee 8.8 ee eeeeeeee ee 8 M M8MM8 eeee. Mee eeeeeee eee eeeeeee eeeee eeee eeeeeeeeeeee eeeeee eee eee eeeeeeeeee eeeee eeeee. Meeee 88 e ee eeeeeeeee (8.88 eee ee eeeeee eeeeeeeee eeeee), eee eeeeeeeeeeeeee eee eeeeeeeee eeee eeeeeee ee eeeeee, eee eee eeee eee eeeeeeee. Meeeeeeee eeeeeeeee eee eeeeeeeeeeee ee eeeeeeee ee e eeeeeeeeeeeeee eeeeeeee ee Me(MM)8 eee eeeeeee ee eeeeeeeeee. e-Meeeeee 8-eeeeeeeee (‌8‌) eee eeee eeeeeeeeeeee ee eeeeeeee ee Me(MM)8 (8.8 eee); eee eeeeeeeee eeeee (888 e) eeeeeeeee 88% eeeeee eeeeeee 8-eeeeeeeee eeeeeeeeeeee (8.88 eee). Meee eeeeeeee eeeeeeeeeee ee e 88% eeeee eeeee ee eeeeee eeeeeeeee eeeee.

Meeeeeeee ee Meeeeee 8-Meeeeeeee (‌Meeee 8‌); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

Me e 888-eM Meeeeeeeee eeeee eeee eeeeeeee eee eeeeeeeee (8.8 eeee), MMM (88 ee, 8.888 eeee), MeMe8 · 8M8M (88 ee, 8.88 eeee), MMe (88 ee, 8.88 eeee), eeeeeeeeeeeeee (88 ee, 8.88 eeee), MeM8 (8.8 ee, 8.88 eeee), eee eeeeeeeeeeee, eeeeeeeee M8M (88 eM). Mee eM ee eee eeee eee eeeeeeee ee 8.8 eeee ee MMM, eee eee eeee eee eeeeeee eeee M8. Meeeeeeeee (88–88 M, eeeeeeeee ee eee eeeeeeeee ee ee eeeeeeeeeeeeee) eee eeeeeeee eeeeee (88–88 M) eeee eeeee. Me eeee eeee (eeeee eeeeee 88 eM), eeeee ee eeeee eeeeeeeeee, e eeeeeeeeeeee eeee ee eeeeeeeeeee eeeeeeee (8.8 eeee; eM 8.8) eee eeeee eeeee e eeeeeee eeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eM eee eeeeeeee ee 8.8, eee Me(MMe)8 (8.8 e, 8.88 eeee) eeeeeeeee ee M8M (8 eM) eee eeeee. Mee eeeeeee eee eeeeeee eee 88 eee eee eeee eeeeeeee ee eeeeee eeeeee eeeeeeeee. Meeeeeee eeeeee eee eeeeeee ee eeeeee Meeee 88M (M+) (88–88 eeeeeeeeee eeeee), eeeeeeee, eee eeeeeeeee. Mee eeee eee eeeeeeee ee eM 8.8 eeee ee MMM eee eeeeeee ee eee eeeee ee eeeeeeeeeeeee ee eee eeeeeeee ee MeMM. Mee eeee eee eeeeeee ee e 888-eM eeeeee ee Meeee 8M8 (MMM8−), eeeee eee eeee eeeeee eeee 88% ee MeMM (888–888 eM), eeeeee eeee 88 eM MM8+MMM8− ee 88% ee MeMM (8 M) ee eeeeee eeeeeeeeeee eeeeee, eee eeee eeeeee eeee 888 eM ee MM8+MMM8− (8 M). Mee eeeeee eeeeee eee eeeeeeeeeeee ee eeeeee eeeeeeeeeee ee 88 °M ee eeeee eee eeeee eeeeeeeee ee eee eeeeeeeeee eeee. Meeeeeeeee eeeeee eee eeeeeeee ee eeeeeeeeee eeeee eeeeeeeeee ee eeeee eeeeeeeeee ee eee(eeeeeeeeeeeeeeeeee) eeeee. Meeeeeeeee eeeee eeee eeeeee ee eeeeeeee eee eeeee eeeeeeeeee ee M8M eeee eeeeee Meeee 88M (M+), eeeeeeeee, eeeeeee eee eM ee eee eeee ee 8.8 eeee ee MeMM, eee eeeeeeee eee eeeeeee ee eeeeee eeeeeeeeeee. Mee(eeeeeeeeeeeeeeeeee) eeeee eeee eeeeee ee eeeeeeeeee eee eeeee eeeeeeeeee ee M8M eeee ee eeeeee ee Meeee 88M (M+), eeeeeeee, eeeeeeeee, eeeeee eeeeeeeeeeeeeee (8 eeeee), eee eeeeeeee eee eeeeeee ee eeeeee eeeeeeeeeee. Mee eee(eeeeeeeeeeeeeeeeee) eeeee eeee eeeeeeeeeeeeee (M8M/eMeMM).

e-Meeeeeeee 8-Meeeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌,‌88‌]

Me e eeee ee eeeeeeeee eeeeeeeeeee eeeeeeee (88%; 88 e, 88 eeee; eM 8) ee M8M (88 eM) ee e 888-eM Meeeeeeeee eeeee eeee eeeee e-eeeeeeeee (88.8 e, 88.8 eeee), MMM (8.88 e, 8.88 eeee, ee eeeeeeee), eee MeMe8 · 8M8M (8.8 e, 88.8 eeee). Mee eM eee eeeeeeee ee 8.8, eee eeee eee eeeeeeee eeee M8 eee 88 eee, eee 8-eeeeeeeeeeeeeee (8.8 eM) eee eeeee. Meeeeeeeee (88 888 M) eee eeeeeeee eeeeee (888 M) eeee eeeeeeeee ee 8 eM ee eee eeeeeee eee eee eeeeee eeee eee eeeeee ee e eeeeeee ee eeeeeeee eeeeee. Mee eeeeee-eeeeeeeeee eee eee eeeee ee eee eeeeeeee eeeee, eeeee eee eeee eeeeeeeee eee eeeeeeee ee 888 eee ee ee eeeeeee eeeeee ee ee. 88M MMM eeeeeeeeeeee eee eeee ee eeeeeee eee eeeeeeeee ee e-eeeeeeeee 8-eeeeeeeee (‌8‌). Meeee 8 e, eeeeeeeeee eeeeeeeeee (88 888 M) ee e eeeeeeee eeeeeeee eee eeeee ee eee eeeeeee. Meeee ee eeeeeeeeee 8 e, eeeeeeeeee (88 888 M), eeeeeeee eeeeee (888 M), eee MeMe8 · 8M8M (888 ee, 8.8 eeee) eeee eeeee. M eeeee eeeeeeeeeee, eeeeeeeeee eee eeeeeeeee eeee ee eeeeeeeee eeeeeeeee, eeeeee eeeeee eee eeeeeeee. Meeee ee eeeeeeeeee 8 e, eee eeeeee-eeeeeeeeee eeee eeee eeeeeee eee eeeeeeee eeeee eeeeeee eeeeeeeeee ee M8M (88 eM). Me eee eeeeeeee eeeeeee eee eeeeeeeeee eee eeeee MeMe8 · 8M8M [8 e, ee 8-e eeeeeeee eeeeeeeee ee M8M (ee. 88 eM)] ee eeeeeeeeeee eeeeeeeee MMM eee eeeeeeeee eeeeeeeee. Meeee eeee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeeee Meeeee eee eeee eeeeee eeee eee eeeeee eeee M8M (ee. 88 eM). MeMe8 · 8M8M (88 e, 88 eeee) eee eeee MeMM (888 eM) eeee eeeee ee eee eeeeeeee eeeeeeeee (888 eM), eee eee eeeeeee eee eeee ee 8 °M eeeeeeeee. Mee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM/M8M (8:8; 888 eM), eee eeeee eeeee eeeeee eeee M8M8 ee eeee eee eeeeee eeee ee ‌8‌; eeeee: 88.8 e (88%; 88% eeeeee). Mee eeee eeeee eeeeeeeee eeeeeeeeeee eeeeeeee (8%) eee eeeeeeeeee (88%).

References