527-50-4

Basic information

• Product Name: L-THREO-PENTULOSE
• Synonyms: L-XYLULOSE;L-THREO-PENTULOSE;L-threo-2-Pentulose (9CI);threo-2-pentulose;(3R,4S)-2-(hydroxymethyl)oxolane-2,3,4-triol;L-Threo-2-pentulose;threo-2-Pentulose, L-threo-Pentulose;L-Xylulose ,98%
• CAS NO: 527-50-4
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• Product Categories: CARBOHYDRATE
• Mol File: 527-50-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 469.1 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: light yellow/syrup
• Density: 1.516g/cm³
• Vapor Pressure: 9.02E-11mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Soluble)
• PKA: 11.90±0.20(Predicted)
• CAS DataBase Reference: L-THREO-PENTULOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-THREO-PENTULOSE(527-50-4)
• EPA Substance Registry System: L-THREO-PENTULOSE(527-50-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 527-50-4(Hazardous Substances Data)

Usage

Chemical Properties

L-xylulose is a clear liquid. It is a ketopentose, meaning that it has five carbon atoms and a ketogroup at carbon C-2. It has a molecular formula of C5H10O5 and a molar mass of 150.13 g/mol. Xylulose is almost colorless and it forms syrup. The formation of crystals has not been reported (Budavari, 1996). Both D- and L - enantiomers of xylulose are found as intermediates in metabolic pathways of prokaryotes as well as eukaryotes. Both forms are rare in nature (Doten and Mortlock, 1985b).

Uses

L-Xylulose is used in studies relating to potential inhibitors of glycosidases and has been proven to inhibit oligosaccharide processing to a degree.

Definition

ChEBI: L-xylulose is a xylulose. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an enantiomer of a D-xylulose.

Application

L-Xylulose has been shown to be a specific inhibitor of certain α-glucosidases,while having virtually no effect on other glycosidases such as β-glucosidase or α- and β-mannosidases. Furthermore,it is a specific inhibitor of the N-linked glycoproteinprocessing enzyme，glucosidase I, but does not inhibit glucosidase I or otherglycoprotein processing mannosidases. Thus it could prove to be a useful inhibitor forstudying glycoprotein processing, especially as it has been proven to be non-toxic andto also be effective in cell cultures (Muniruzzaman et al., 1996). L-Xylulose has been shown to have a strong inhibitory effect on the a-glucosidases，sucrase and maltase, present in the small intestine. Thus, an L-xylulose containing drug preparation for reducing blood sugar levels in humans and animals has been patented (Heinz et al.,1998).

Preparation

In 1933 a synthetic procedure for producing small amounts of D- and L -xylulose was introduced. In this method D- or L-xylose is epimerized to the corresponding diastereomer. The isomerization of xylose in pyridine leads to the production of xylulose (Touster, 1962). This enzyme catalyzes the production of L-xylulose from xylitol using either PQQ (pyrroloquinoline quinone) or FAD (flavin adenine dinucleotide) as prosthetic group, and L-xylulose is accumulated in the medium (Adachi et al., 1999; Adachi et al., 2001).

InChI:InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5-/m0/s1

Upstream product

• 488-82-4 D-Arabitol 
• 96-26-4 dihydroxyacetone 
• 141-46-8 Glycolaldehyde 
• 87-99-0 XYLITOL 
• 7558-89-6 ribulose 
• 67-64-1 acetone 
• 488-81-3 Adonitol 
• 1114-34-7 D-lyxose 
• 10323-20-3 D-Arabinose 
• 58-86-6 D-xylose 
• 50-69-1 D-ribose 
• 526-97-6 D-gluconic acid 

Downstream Products

• 87-99-0 XYLITOL 

Relevant articles and documents

Production of keto-pentoses: Via isomerization of aldo-pentoses catalyzed by phosphates and recovery of products by anionic extraction

Xylulose and ribulose are rare keto-pentoses which are in high demand for the synthesis of commodities and fine chemicals. The production of keto-pentoses via isomerization of aldo-pentoses presents a carbon-efficient synthetic method. However, the isomerizations are equilibrium processes with thermodynamically limited yields of the products. In this work we examined isomerization of aldo-pentoses into keto-pentoses in the presence of NaH2PO4 + Na2HPO4 as a soluble catalyst at pH 7.5. A reaction network was proposed based on product distribution with d-(1-13C)-ribose as a substrate. Additionally, kinetics of the isomerization reactions was addressed. Selectivity for the keto-pentoses dramatically depends on the structure of the substrate. Arabinose and xylose give rise to a number of isomeric pentoses with low selectivities for the target products. Investigation of the reaction kinetics suggests that xylose and arabinose slowly isomerize into xylulose and ribulose, respectively. The latter react further significantly quicker to produce a number of isomers as subsequent products. This causes a complex mixture of products with low selectivity for the keto-pentoses. In contrast, ribose and lyxose as substrates yield ribulose and xylulose with rather high selectivities of 68-79% at 20% conversion. Ribose and lyxose quickly isomerize into ribulose and xylulose, respectively, whereas the subsequent processes are relatively slow. This results in a high selectivity for the keto-pentoses based on ribose and lyxose. Moreover, the isolation of xylulose from the reaction mixture was also studied. Xylulose can be selectively recovered after the isomerization of lyxose using anionic extraction with o-hydroxymethyl phenylboronic acid (HMPBA). After extraction, the aqueous phase containing phosphates and remaining lyxose can be recycled. After four cycles, the yield of xylulose reached 37% though only 19% can be achieved under batch conditions. Xylulose can be further recovered from the organic phase by back extraction using an acidified solution. Ribulose can also be extracted as an anionic complex with HMPBA, though ribose is co-extracted in this case and a separation of ribulose from ribose cannot be achieved. Extraction of the keto-pentoses occurs due to formation of β-xylulose-HMPBA and α-ribulose-HMPBA anionic complexes, whose molecular structures were established by NMR and MS.

Aldol Reaction between Small Sugars. Preparation of DL-threo-2-Pentulose and DL-lyxo-3-Hexulose and their Isolation as O-Isopropylidene Derivatives

The improved diastereoselectivity obtained with strongly basic anion-exchange resin as catalyst in aldol condensation between two-, three- and four-carbon "sugars" has been utilised in the preparation of DL-threo-2-pentulose and DL-lyxo-3-hexulose, which were isolated as their O-isopropylidene derivatives.A possible reason for the observe preference of formation of the lyxo-diastereomer in condensation between glycolaldehyde and glycero-tetrulose is suggested.

Kinetics, Catalysis, and Mechanism of the Secondary Reaction in the Final Phase of the Formose Reaction

In the final phase of the formose reaction sugars are formed by the reaction of glycolaldehyde, glyceraldehyde and dihydroxyacetone.The application of high-pressure liquid chromatography allows for the first time to investigate intermediate and final products quantitatively.The results of kinetical investigations allow to suggest a reaction mechanism for the secondary reaction in the final phase of the formose reaction.This mechanism is compared with that of the starting phase and other known mechanisms.From the results metal ion-catalyzed aldol reactions have to be assumed.