L-Rhamnose

CAS# 6155-35-7

L-Rhamnose

2D Structure

Catalog No. BCN6302----Order now to get a substantial discount!

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Quality Control of L-Rhamnose

3D structure

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L-Rhamnose

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Chemical Properties of L-Rhamnose

Cas No. 6155-35-7 SDF Download SDF
PubChem ID 22856332 Appearance White cryst.
Formula C6H14O6 M.Wt 182.17
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility H2O : 100 mg/mL (548.94 mM; Need ultrasonic and warming)
Chemical Name (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol;hydrate
SMILES CC1C(C(C(C(O1)O)O)O)O.O
Standard InChIKey BNRKZHXOBMEUGK-NRBMBCGPSA-N
Standard InChI InChI=1S/C6H12O5.H2O/c1-2-3(7)4(8)5(9)6(10)11-2;/h2-10H,1H3;1H2/t2-,3-,4+,5+,6+;/m0./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of L-Rhamnose

The flowers of Scphora japonica L.

Biological Activity of L-Rhamnose

DescriptionL-Rhamnose may exhibit excellent sodium-glucose transporter (SGLT1 and SGLT2) inhibition activity. L-fucose and especially L-rhamnose have anticancer potential, they exert a significant suppressive effect on tumour growth.
TargetsSGLT
In vivo

L-Rhamnose increases serum propionate after long-term supplementation, but lactulose does not raise serum acetate.[Pubmed: 15531673]

Am J Clin Nutr. 2004 Nov;80(5):1254-61.

Acute ingestion of the unabsorbed sugar L-Rhamnose in humans raises serum propionate, whereas acute ingestion of lactulose raises serum acetate. It is not known whether short-chain fatty acid concentrations in urine and feces reflect those in blood. The objective was to test the effects of oral L-Rhamnose and lactulose for 28 d on acetate and propionate concentrations in serum, urine, and feces.
METHODS AND RESULTS:
Eleven subjects ingested 25 g L-Rhamnose, lactulose, or d-glucose (control) for 28 d in a partially randomized crossover design. One fecal sample, hourly blood samples, and all urine samples were collected over 12 h on the last day of each phase. The increase in serum propionate was greater after L-Rhamnose than after lactulose (P < 0.05). The effect of lactulose on serum acetate was not significant, but lactulose raised the acetate:propionate ratio compared with d-glucose or L-Rhamnose in serum (P < 0.005) and urine (P < 0.02). Flatulence was significantly greater after lactulose and L-Rhamnose than after d-glucose (P < 0.0001), an effect that lasted 4 wk with lactulose but only 1 wk with L-Rhamnose.
CONCLUSIONS:
This study confirmed that L-Rhamnose ingestion over 28 d continues to selectively raise serum propionate in humans. Although serum acetate did not increase significantly after lactulose, the serum acetate:propionate ratio was significantly different after L-Rhamnose and lactulose, which suggests that these substrates could be used to examine the role of colonic acetate and propionate production in the effect of dietary fiber on lipid metabolism. Changes in the ratio of urinary acetate to propionate reflected those in serum.

L-rhamnose and L-fucose suppress cancer growth in mice.[Reference: WebLink]

Cent. Eur. J. Biol., 2011, 6(1):1-9.

It is documented that deficient fucosylation may play an important role in the pathogenesis of cancer. Since the supplementation of L-fucose could restore fucosylation in both in vitro and in vivo conditions, our intent was to examine the effect of intraperitoneal administration of L-fucose and L-Rhamnose (a similar deoxysaccharide) on tumour growth, mitotic activity and metastatic setting of a solid form of Ehrlich carcinoma as well as on the survival rate of tumour bearing mice.
METHODS AND RESULTS:
Both L-fucose and L-Rhamnose exerted a significant suppressive effect on tumour growth (P<0.05). After 10 days of therapy, the greatest inhibition of tumour growth expressed as a percentage of controls was observed in L-Rhamnose at a dose of 3 g/kg/day (by 62%) and L-fucose at a dose of 5 g/kg/day (by 47%). Moreover, the mitotic index decreased with increasing doses of L-fucose and L-Rhamnose. Prolonged survival of tumour bearing mice was observed after 14 consecutive days of daily administering L-Rhamnose. Its optimal dose was estimated to be 3.64 g/kg/day. L-Fucose, however, displayed only a slight effect on the survival of the mice.
CONCLUSIONS:
Our results suggest that L-fucose and especially L-Rhamnose have anticancer potential. This study is the first to demonstrate the tumour-inhibitory effect of L-Rhamnose.

Protocol of L-Rhamnose

Kinase Assay

The Aspergillus nidulans Zn(II)2Cys6 transcription factor AN5673/RhaR mediates L-rhamnose utilization and the production of α-L-rhamnosidases.[Pubmed: 25416526]

Microb Cell Fact. 2014 Nov 22;13(1):161.

Various plant-derived substrates contain L-Rhamnose that can be assimilated by many fungi and its liberation is catalyzed by α-L-rhamnosidases.Whilst induction is effected by L-Rhamnose, unlike many other glycosyl hydrolase genes repression by glucose and other carbon sources occurs in a manner independent of CreA.
METHODS AND RESULTS:
To date regulatory genes affecting L-Rhamnose utilization and the production of enzymes that yield L-Rhamnose as a product have not been identified in A. nidulans. In this study we have identified the rhaR gene in A. nidulans and Neurospora crassa (AN5673, NCU9033) encoding a putative Zn(II)2Cys6 DNA-binding protein. Genetic evidence indicates that its product acts in a positive manner to induce transcription of the A. nidulans L-Rhamnose regulon. rhaR-deleted mutants showed reduced ability to induce expression of the α-L-rhamnosidase genes rhaA and rhaE and concomitant reduction in α-L-rhamnosidase production. The rhaR deletion phenotype also results in a significant reduction in growth on L-Rhamnose that correlates with reduced expression of the L-rhamnonate dehydratase catabolic gene lraC (AN5672). Gel mobility shift assays revealed RhaR to be a DNA binding protein recognizing a partially symmetrical CGG-X11-CCG sequence within the rhaA promoter. Expression of rhaR alone is insufficient for induction since its mRNA accumulates even in the absence of L-Rhamnose, therefore the presence of both functional RhaR and L-Rhamnose are absolutely required. In N. crassa, deletion of rhaR also impairs growth on L-Rhamnose.
CONCLUSIONS:
To define key elements of the L-Rhamnose regulatory circuit, we characterized a DNA-binding Zn(II)2Cys6 transcription factor (RhaR) that regulates L-Rhamnose induction of α-L-rhamnosidases and the pathway for its catabolism in A. nidulans, thus extending the list of fungal regulators of genes encoding plant cell wall polysaccharide degrading enzymes. These findings can be expected to provide valuable information for modulating α-L-rhamnosidase production and L-Rhamnose utilization in fungi and could eventually have implications in fungal pathogenesis and pectin biotechnology.

Structure Identification
Org Biomol Chem. 2014 Nov 14;12(42):8415-21.

Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors.[Pubmed: 25175761]


METHODS AND RESULTS:
Herein we describe the synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-Rhamnose. The key reactions involved are (i) Zn(OTf)2 catalyzed enantioselective alkynylation of L-Rhamnose derived azidoaldehyde and (ii) deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols.
CONCLUSIONS:
Some compounds exhibit excellent sodium-glucose transporter (SGLT1 and SGLT2) inhibition activity.

Infect Immun. 1989 Jun;57(6):1691-6.

Heterogeneity of the L-rhamnose residue in the outer core of Pseudomonas aeruginosa lipopolysaccharide, characterized by using human monoclonal antibodies.[Pubmed: 2498204 ]


METHODS AND RESULTS:
Hybridoma cell lines producing human monoclonal antibodies (MAbs) MH-4H7 and KN-2B11 [immunoglobulin M (lambda)] which bound to the outer core region of Pseudomonas aeruginosa lipopolysaccharide (LPS) were established by cell fusion of human peripheral lymphocytes with human-mouse heteromyeloma SHM D-33. Both binding specificity experiments with a series of LPS-defective mutants derived from P. aeruginosa PAC1R (P. S. N. Rowe and P. M. Meadow, Eur. J. Biochem.132:329-337, 1983) and competitive enzyme immunoassay experiments with monosaccharides demonstrated that alpha-L-Rhamnose residues in the outer core of LPS might be in part an epitope. The MAbs specifically bound to clinical isolates belonging to Homma serotypes A, F, G, and K at a frequency of 70 to 86% and to serotypes H and M isolates at about 50%. They did not bind to any isolates of serotype B, E, and I tested.
CONCLUSIONS:
This evidence indicates that L-Rhamnose and probably its neighboring residues in the other core of P. aeruginosa are heterogeneous in some association with the O serotype.

L-Rhamnose Dilution Calculator

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Preparing Stock Solutions of L-Rhamnose

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.4894 mL 27.4469 mL 54.8938 mL 109.7876 mL 137.2345 mL
5 mM 1.0979 mL 5.4894 mL 10.9788 mL 21.9575 mL 27.4469 mL
10 mM 0.5489 mL 2.7447 mL 5.4894 mL 10.9788 mL 13.7234 mL
50 mM 0.1098 mL 0.5489 mL 1.0979 mL 2.1958 mL 2.7447 mL
100 mM 0.0549 mL 0.2745 mL 0.5489 mL 1.0979 mL 1.3723 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on L-Rhamnose

Heterogeneity of the L-rhamnose residue in the outer core of Pseudomonas aeruginosa lipopolysaccharide, characterized by using human monoclonal antibodies.[Pubmed:2498204]

Infect Immun. 1989 Jun;57(6):1691-6.

Hybridoma cell lines producing human monoclonal antibodies (MAbs) MH-4H7 and KN-2B11 [immunoglobulin M (lambda)] which bound to the outer core region of Pseudomonas aeruginosa lipopolysaccharide (LPS) were established by cell fusion of human peripheral lymphocytes with human-mouse heteromyeloma SHM D-33. Both binding specificity experiments with a series of LPS-defective mutants derived from P. aeruginosa PAC1R (P. S. N. Rowe and P. M. Meadow, Eur. J. Biochem.132:329-337, 1983) and competitive enzyme immunoassay experiments with monosaccharides demonstrated that alpha-L-Rhamnose residues in the outer core of LPS might be in part an epitope. The MAbs specifically bound to clinical isolates belonging to Homma serotypes A, F, G, and K at a frequency of 70 to 86% and to serotypes H and M isolates at about 50%. They did not bind to any isolates of serotype B, E, and I tested. This evidence indicates that L-Rhamnose and probably its neighboring residues in the other core of P. aeruginosa are heterogeneous in some association with the O serotype.

The Aspergillus nidulans Zn(II)2Cys6 transcription factor AN5673/RhaR mediates L-rhamnose utilization and the production of alpha-L-rhamnosidases.[Pubmed:25416526]

Microb Cell Fact. 2014 Nov 22;13:161.

BACKGROUND: Various plant-derived substrates contain L-Rhamnose that can be assimilated by many fungi and its liberation is catalyzed by alpha-L-rhamnosidases. Initial data obtained in our laboratory focussing on two Aspergillus nidulans alpha-L-rhamnosidase genes (rhaA and rhaE) showed alpha-L-rhamnosidase production to be tightly controlled at the level of transcription by the carbon source available. Whilst induction is effected by L-Rhamnose, unlike many other glycosyl hydrolase genes repression by glucose and other carbon sources occurs in a manner independent of CreA. To date regulatory genes affecting L-Rhamnose utilization and the production of enzymes that yield L-Rhamnose as a product have not been identified in A. nidulans. The purpose of the present study is to characterize the corresponding alpha-L-rhamnosidase transactivator. RESULTS: In this study we have identified the rhaR gene in A. nidulans and Neurospora crassa (AN5673, NCU9033) encoding a putative Zn(II)2Cys6 DNA-binding protein. Genetic evidence indicates that its product acts in a positive manner to induce transcription of the A. nidulans L-Rhamnose regulon. rhaR-deleted mutants showed reduced ability to induce expression of the alpha-L-rhamnosidase genes rhaA and rhaE and concomitant reduction in alpha-L-rhamnosidase production. The rhaR deletion phenotype also results in a significant reduction in growth on L-Rhamnose that correlates with reduced expression of the L-rhamnonate dehydratase catabolic gene lraC (AN5672). Gel mobility shift assays revealed RhaR to be a DNA binding protein recognizing a partially symmetrical CGG-X11-CCG sequence within the rhaA promoter. Expression of rhaR alone is insufficient for induction since its mRNA accumulates even in the absence of L-Rhamnose, therefore the presence of both functional RhaR and L-Rhamnose are absolutely required. In N. crassa, deletion of rhaR also impairs growth on L-Rhamnose. CONCLUSIONS: To define key elements of the L-Rhamnose regulatory circuit, we characterized a DNA-binding Zn(II)2Cys6 transcription factor (RhaR) that regulates L-Rhamnose induction of alpha-L-rhamnosidases and the pathway for its catabolism in A. nidulans, thus extending the list of fungal regulators of genes encoding plant cell wall polysaccharide degrading enzymes. These findings can be expected to provide valuable information for modulating alpha-L-rhamnosidase production and L-Rhamnose utilization in fungi and could eventually have implications in fungal pathogenesis and pectin biotechnology.

L-Rhamnose increases serum propionate after long-term supplementation, but lactulose does not raise serum acetate.[Pubmed:15531673]

Am J Clin Nutr. 2004 Nov;80(5):1254-61.

BACKGROUND: Acute ingestion of the unabsorbed sugar L-Rhamnose in humans raises serum propionate, whereas acute ingestion of lactulose raises serum acetate. It is not known whether short-chain fatty acid concentrations in urine and feces reflect those in blood. OBJECTIVE: The objective was to test the effects of oral L-Rhamnose and lactulose for 28 d on acetate and propionate concentrations in serum, urine, and feces. DESIGN: Eleven subjects ingested 25 g L-Rhamnose, lactulose, or d-glucose (control) for 28 d in a partially randomized crossover design. One fecal sample, hourly blood samples, and all urine samples were collected over 12 h on the last day of each phase. RESULTS: The increase in serum propionate was greater after L-Rhamnose than after lactulose (P < 0.05). The effect of lactulose on serum acetate was not significant, but lactulose raised the acetate:propionate ratio compared with d-glucose or L-Rhamnose in serum (P < 0.005) and urine (P < 0.02). Flatulence was significantly greater after lactulose and L-Rhamnose than after d-glucose (P < 0.0001), an effect that lasted 4 wk with lactulose but only 1 wk with L-Rhamnose. CONCLUSIONS: This study confirmed that L-Rhamnose ingestion over 28 d continues to selectively raise serum propionate in humans. Although serum acetate did not increase significantly after lactulose, the serum acetate:propionate ratio was significantly different after L-Rhamnose and lactulose, which suggests that these substrates could be used to examine the role of colonic acetate and propionate production in the effect of dietary fiber on lipid metabolism. Changes in the ratio of urinary acetate to propionate reflected those in serum.

Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors.[Pubmed:25175761]

Org Biomol Chem. 2014 Nov 14;12(42):8415-21.

Herein we describe the synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-Rhamnose. The key reactions involved are (i) Zn(OTf)2 catalyzed enantioselective alkynylation of L-Rhamnose derived azidoaldehyde and (ii) deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols. Some compounds exhibit excellent sodium-glucose transporter (SGLT1 and SGLT2) inhibition activity.

Description

α-L-Rhamnose monohydrate is a component of the plant cell wall pectic polysaccharides rhamnogalacturonan I and rhamnogalacturonan II. α-L-Rhamnose monohydrate is also a component of bacterial polysaccharides where it plays an important role in pathogenicity.

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