16203-27-3

Upstream product

• 56650-22-7 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 133-89-1 UDP-glucose 
• 15356-70-4 menthol 
• 2216-51-5 (-)-menthol 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 79466-08-3 (-)-Menthol glucuronide 
• 67462-22-0 (-)-menthol α-D-glucoside 
• 2216-51-5 (-)-menthol 

Relevant academic research and scientific papers

Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation

Menthol has a considerable cooling effect, but the use range of menthol is limited because of its extremely low solubility in water and inherent flavor. (?)-Menthol β-glucoside was determined to be more soluble in water (>27 times) than (?)-menthol α-glucoside; hence, β-anomer-selective glucosylation of menthol is necessary. The in vitro glycosylation of (?)-menthol by uridine diphosphate glycosyltransferase (BLC) from Bacillus licheniformis generated (?)-menthol β-glucoside and new (?)-menthol β-galactoside and (?)-menthol N-acetylglucosamine. The maximum conversion rate of menthol to (?)-menthol β-d-glucoside by BLC was found to be 58.9%. Importantly, (?)-menthol β-d-glucoside had a higher cooling effect and no flavor compared with menthol. In addition, (?)-menthol β-d-glucoside was determined to be a non-sensitizer in a skin allergy test in the human cell line activation test, whereas menthol was a sensitizer.

Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

It was established that para-substituted benzyl ether protecting groups affect the reactivity of glycosyl donors of the thioglycoside type with the N-iodosuccinimide/triflic acid promoter system. Having electron donating p-methoxybenzyl ether (PMB) groups increased the reactivity of the donor in comparison to having electron withdrawing p-chloro (PClB) or p-cyanobenzyl ether (PCNB) protecting groups, which decreased the reactivity of the glycosyl donor relative to the parent benzyl ether (Bn) protected glycosyl donor. These findings were used to perform the first armed-disarmed coupling between two benzylated glucosyl donors by tuning their reactivity. In addition, the present work describes a highly efficient palladium catalyzed multiple cyanation and methoxylation of p-chlorobenzyl protected thioglycosides. The results of this paper regarding both the different electron withdrawing properties of various benzyl ethers and the efficient and multiple protecting group transformations are applicable in general organic chemistry and not restricted to carbohydrate chemistry.

Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

Two glucosyltransferases were isolated from plant cell cultures of Catharanthus roseus and Nicotiana tabacum. The enzyme from C. roseus enantioselectively glucosylated (±)-secondary alcohols to give the glucosides of (R)-alcohols, while the glucosylation with that from N. tabacum gave preferentially the glucosides of (S)-alcohols.

Inhibitory effects of perillosides A and C, and related monoterpene glucosides on aldose reductase and their structure-activity relationships.

Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent typ