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Please login to access the full content or check if you have access via2.1.2.1.2.3 Aldol Addition of 1,3-Dihydroxyacetone Phosphate to Thiol-Containing Aldehydes
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Clapés, P., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 41.
Similar to hydroxyaldehydes, thiol substitution in the aldehyde component for aldolase catalysis furnishes products that can cyclize to form rather stable cyclic thiohemiacetal structures. Such thiosugars are a structural variation of carbohydrates that possess interesting biological properties such as glycosidase inhibition.[58] The observed unbiased stereoselectivity in the enzymatic aldol addition reactions indicates the full equivalence of hydroxy and thiol substituents for correct substrate recognition (Scheme 14).[59,60] Most of the starting sulfanylaldehydes are dimers with both low water solubility and monomer content in solution, which makes an effective addition difficult, particularly when dealing with poor acceptors having high KM values.
Meeeee 88 Meeee Meeeeeee ee 8,8-Meeeeeeeeeeeeeee Meeeeeeee ee Meeee-Meeeeeeeee Meeeeeeee[88,88]
| M8 | Meeeeee | Meeee (eee/eeee) | Meeee (%) | Mee |
|---|---|---|---|---|
| MM8MM | MeeM | >88:8 | 88 | [88] |
 |
MeeM | >88:8 | 88 | [88] |
| |
MeeM | 8:>88 | 88 | [88] |
| |
MeeM | >88:8 | 88 | [88] |
e MeeM eeee eeeeee eeeeee (MMMM); MeeM eee MeeM eeee M. eeee.
M eeee eeeeeeeeee eeeeeeee ee ee eeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeee eeeeeeeeee (e.e., 88) ee eeee, ee eeeee ee Meeeee 88 eee eee eeeeeeeee ee 8-eeee-e-eeeeeeee (88) eeeeeeee eeee (M)-eeeeeeeeeeeeee eeeeeee eeeeee (8) eee (M)-M-eeeeee-8-eeeeeeeeeeeeeeeeee eeeeeee eeeeee (88).[88] Meeeeeeeeee, ee eeee ee eeeeeeeeee eeee eee eeeee eeeeeeee ee eeeeeeeee ee eeeeeeee eee eeee eeee eeeeeee eee eeeeeeeeeee ee eeee eeeeee. Me eeeee eeeeeeee ee 8-eeeeee- ee 8-eeeeeeeeeeeeeeeee eeeeeeee ee eeeeeeeeeeee eeeeeee eeeeeeeeeeee ee eee eeeeee eeeeeeeeee e eeeeee eeeeeeeeeee eeeee ee eeeeee eeeeeeeeee.[88]
Meeeeeeee eeeeeeeeeeee eeeeeeeeee eee eeeee ee Meeeeee ee Meeeeeeee: Meeeeeeeeeeeeee Meeeeeeee [Meeeeeeeeeeeeee Meeeeeeee ee Meeeeeee eee Meeee Meeeee (Meeeeee 8.88.8.8)].
Meeeee 88 Meeeeeeeeee ee 8-Meee-e-eeeeeeee[88]
References
| [58] | Meeeeee, M. M.; Meeeeee, M. M., Meee. Meeeeeeee. Meeeeeeeee., (8888) 88, 888. |
| [59] | Meeeeeeeeee, M.; Meeeee, M.; Meee, M., Meeeeee Mee. Meee., (8888), 8888. |
| [60] | Meee, M.-M.; Meee, M.; Meee, M.-M.; Meee, M.-M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [61] | Meeeeeeeeee, M.; Meeeee, M.; Méeeeee, M.; Meeeeee, M.; Meeeeee, M., Mee. M. Mee. Meee., (8888), 8888. |
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