125279-72-3

Usage

Uses

Used in Pharmaceutical Industry:
Lentiginosine is used as an inhibitor for its ability to selectively and powerfully inhibit amyloglucosidases, which can be beneficial in the development of treatments for certain medical conditions.
Used in Biochemical Research:
In the field of biochemical research, lentiginosine is utilized as a research tool to study the function and regulation of amyloglucosidases, contributing to a better understanding of their role in various biological processes.
Used in Food Industry:
Lentiginosine may also find applications in the food industry as an additive or preservative, where its ability to inhibit amyloglucosidases could be leveraged to control the breakdown of starches and extend the shelf life of certain products.

InChI:InChI=1/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m1/s1

Upstream product

• 119795-71-0 (-)-(1R,2R,8aR)-1,2-(isopropylidenedioxy)-1,5,6,7,8,8ahexahydro-2H-indolizin-3-one 
• 119795-70-9 (1R,2R,8aR)-1,2-(isopropylidenedioxy)-1,5,6,8a-tetrahydro-3(2H)-indolizinone 
• 119795-69-6 (3R,4S)-1-<(Z)-4-(trimethylsilyl)-3-butenyl>-3,4-(isopropylidenedioxy)-5-acetoxypyrrolidin-2-one 
• 359866-28-7 (1S,2S,8aS)-1,2-(isopropylidenedioxy)-1,5,6,7,8,8a-hexahydro-3(2H)-indolizinone 
• 570385-49-8 (3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 108796-03-8 (1-methoxycarbonyl)-2-(4-bromobutyl)-3-pyrroline 
• 501939-11-3 (1S,2S,8aR)-(-)-1,2-dihydroxy-1,2,3,5,8,8a-hexahydroindolizine 
• 501939-12-4 (3R,4R)-4-(acetyloxy)-1-allyl-5-hydroxy-2-oxopyrrolidin-3-yl acetate 
• 184774-88-7 (3R,4R)-4-(acetyloxy)-1-allyl-2,5-dioxopyrrolidin-3-yl acetate 
• 501939-10-2 (1S,2S,8aS)-(-)-1,2-dihydroxy-1,2,3,5,8,8a-hexahydroindolizine 
• 952057-08-8 C₁₂H₁₇NO₅ 
• 220875-15-0 (5S,6S,7R)-1,2-diaza-6-benzyloxy-7-hydroxy-3-oxo-[3.3.0]bicyclooctane 
• 3105-95-1 pipecolinic acid 
• 160169-49-3 (1R,2S,8aR)-1,2-dihydroxy-hexahydroindolizin-3(5H)-one 

Relevant academic research and scientific papers

New concise total synthesis of (+)-lentiginosine and some structural analogues

An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

A Stereoselective Synthesis of Lentiginosine

A concise stereoselective synthesis of (-)-lentiginosine, an iminosugar endowed with an interesting proapoptotic activity, has been accomplished using an enantiopure pyrroline N-oxide building block derived from d-tartaric acid. Key steps are a totally diastereoselective nucleophilic addition to the cyclic nitrone followed by a combination of two simultaneous and two tandem reactions occurring under the same conditions in a single laboratory operation. Natural (+)-lentiginosine can be synthesized by the same method but starting from l-tartaric acid. (Chemical Equation Presented).

Structure-guided engineering of D-fructose-6-phosphate aldolase for improved acceptor tolerance in biocatalytic aldol additions

Abstract A structure-guided redesign of D-fructose-6-phosphate aldolase from Escherichia coli (FSA) was devised for improving the acceptor tolerance towards α-substituted and conformationally constrained aldehydes. FSA A129S/R134X/A165G/S166G and L107Y/A1

Total syntheses of (±)-lentiginosine and (±)-1-epi-lentiginosine from hexahydro-1H-indol-3-one

Total syntheses of (±)-lentiginosine 1 and (±)-1-epi-lentiginosine 2 were achieved efficiently from hexahydro-1H-indol-3-one 7.

Enhanced trans diastereoselection in the allylation of cyclic chiral N-acyliminium ions. Synthesis of hydroxylated indolizidines

A short synthesis of hydroxylated indolizidines is reported. The key steps were the allylation of chiral cyclic N-acyliminium ions derived from malic and tartaric acids, followed by ring-closing metathesis.

Synthesis of Natural Lentiginosine Employing a Cyclic Imide with C2-Symmetry Derived from L-Tartaric Acid

The first efficient and simple process is described for the synthesis of a new (1S,2S,8aS)-1,2-dihydroxyindolizidine alkaloid, lentiginosine.The synthetic strategy is based on asymmetric deoxygenation of the quarternary α-hydroxy lactam prepared from a C

A novel concise total synthesis of (+)-lentiginosine

A total synthesis of (+)-lentiginosine was achieved by using ethyl 3-(pyridin-2-yl)acrylate N-oxide as the starting material and an improved Sharpless asymmetric dihydroxylation as the key step.

Synthesis of 1,2-dihydroxyindolizidines from 1-(2-pyridyl)-2-propen-1-ol

1-(2-Pyridyl)-2-propen-1-ol, obtained by vinylation of commercially available picolinaldehyde, resulted a good starting material for the synthesis of the indolizidine skeleton. In particular, a simple process involving bromination, reduction, and nucleophilic substitution (via elimination and addition) allowed an easy conversion of the starting material into (±)-lentiginosine in ～27% overall yield.

Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.

Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols

Palladium-catalyzed allylic substitution of non-derivatized enantioenriched allylic alcohols with a variety of uncharged N-, S-, C- and O-centered nucleophiles using a bidentate BiPhePhos ligand is described. A remarkable effect of the counter ion (X) of the XPd[κ2-BiPhePhos][η3-C3H5] was observed. When ClPd[κ2-BiPhePhos][η3-C3H5] (complex I) was used as catalyst, non-reproducible results were obtained. Study of the complex by X-ray crystallography, 31P NMR spectroscopy, and ESI-MS showed that a decomposition occurred where one of the phosphite ligands was oxidized to the corresponding phosphate, generating ClPd[κ1-BiPhePhosphite-phosphate][η3-C3H5] species (complex II). When the chloride was exchanged to the weaker coordinating OTf? counter ion the more stable Pd[κ2-BiPhePhos][η3-C3H5]++[OTf] ? (complex III) was formed. Complex III performed better and gave higher enantiospecificities in the substitution reactions. Complex III was evaluated in Tsuji–Trost reactions of stereogenic non-derivatized allylic alcohols. The desired products were obtained in good to excellent yields (71–98 %) and enantiospecificities (73–99 %) for both inter- and intramolecular substitution reactions with only water generated as a by-product. The methodology was applied to key steps in total synthesis of (S)-cuspareine and (+)-lentiginosine. A reaction mechanism involving a palladium hydride as a key intermediate in the activation of the hydroxyl group is proposed in the overall transformation.