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MedKoo Cat#: 599136 | Name: Rhamnose

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rhamnose is a methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides.

Chemical Structure

Rhamnose
Rhamnose
CAS#3615-41-6

Theoretical Analysis

MedKoo Cat#: 599136

Name: Rhamnose

CAS#: 3615-41-6

Chemical Formula: C6H12O5

Exact Mass: 164.0685

Molecular Weight: 164.15

Elemental Analysis: C, 43.90; H, 7.37; O, 48.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rhamnose; L-Rhamnose; NSC 2056; NSC-2056; NSC2056; Isodulcitol; Isodulcit; Locaose; Mannomethylose, L-;
IUPAC/Chemical Name
(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
InChi Key
PNNNRSAQSRJVSB-BXKVDMCESA-N
InChi Code
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1
SMILES Code
O[C@H]([C@H](O)[C@H]([C@@H](O)C)O)C=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 164.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Sheridan RT, Hudon J, Hank JA, Sondel PM, Kiessling LL. Rhamnose glycoconjugates for the recruitment of endogenous anti-carbohydrate antibodies to tumor cells. Chembiochem. 2014 Jul 7;15(10):1393-8. doi: 10.1002/cbic.201402019. Epub 2014 Jun 6. PubMed PMID: 24909955; PubMed Central PMCID: PMC4205123. 2: Carneiro RF, Teixeira CS, de Melo AA, de Almeida AS, Cavada BS, de Sousa OV, da Rocha BA, Nagano CS, Sampaio AH. L-Rhamnose-binding lectin from eggs of the Echinometra lucunter: Amino acid sequence and molecular modeling. Int J Biol Macromol. 2015;78:180-8. doi: 10.1016/j.ijbiomac.2015.03.072. Epub 2015 Apr 14. PubMed PMID: 25881955. 3: Lu L, Liu Q, Jin L, Yin Z, Xu L, Xiao M. Enzymatic Synthesis of Rhamnose Containing Chemicals by Reverse Hydrolysis. PLoS One. 2015 Oct 27;10(10):e0140531. doi: 10.1371/journal.pone.0140531. eCollection 2015. PubMed PMID: 26505759; PubMed Central PMCID: PMC4624630. 4: Liang J, Aleksanyan H, Metzenberg S, Oppenheimer SB. Involvement of l(-)-rhamnose in sea urchin gastrulation. Part II: α-l-Rhamnosidase. Zygote. 2016 Jun;24(3):371-7. doi: 10.1017/S0967199415000283. Epub 2015 Jul 14. PubMed PMID: 26168775. 5: Han X, Qian L, Zhang L, Liu X. Structural and biochemical insights into nucleotide-rhamnose synthase/epimerase-reductase from Arabidopsis thaliana. Biochim Biophys Acta. 2015 Oct;1854(10 Pt A):1476-86. doi: 10.1016/j.bbapap.2015.06.007. Epub 2015 Jun 23. PubMed PMID: 26116145. 6: Jordan DS, Daubenspeck JM, Dybvig K. Rhamnose biosynthesis in mycoplasmas requires precursor glycans larger than monosaccharide. Mol Microbiol. 2013 Sep;89(5):918-28. doi: 10.1111/mmi.12320. Epub 2013 Jul 19. PubMed PMID: 23826905; PubMed Central PMCID: PMC3771393. 7: Smith TN, Oppenheimer SB. Involvement of L(-)-rhamnose in sea urchin gastrulation: a live embryo assay. Zygote. 2015 Apr;23(2):222-8. doi: 10.1017/S0967199413000452. Epub 2013 Oct 18. PubMed PMID: 24134935. 8: Gruben BS, Zhou M, Wiebenga A, Ballering J, Overkamp KM, Punt PJ, de Vries RP. Aspergillus niger RhaR, a regulator involved in L-rhamnose release and catabolism. Appl Microbiol Biotechnol. 2014 Jun;98(12):5531-40. doi: 10.1007/s00253-014-5607-9. Epub 2014 Feb 28. PubMed PMID: 24682478. 9: McCaughey LC, Grinter R, Josts I, Roszak AW, Waløen KI, Cogdell RJ, Milner J, Evans T, Kelly S, Tucker NP, Byron O, Smith B, Walker D. Lectin-like bacteriocins from Pseudomonas spp. utilise D-rhamnose containing lipopolysaccharide as a cellular receptor. PLoS Pathog. 2014 Feb 6;10(2):e1003898. doi: 10.1371/journal.ppat.1003898. eCollection 2014 Feb. PubMed PMID: 24516380; PubMed Central PMCID: PMC3916391. 10: Zamlynska K, Komaniecka I, Turska-Szewczuk A, Pac M, Choma A. The O-specific polysaccharides from Phyllobacterium trifolii PETP02(T) LPS contain 3-C-methyl-D-rhamnose. Carbohydr Res. 2015 May 29;409:25-9. doi: 10.1016/j.carres.2015.02.013. Epub 2015 Mar 6. PubMed PMID: 25917130. 11: Long DE, Karmakar P, Wall KA, Sucheck SJ. Synthesis of α-L-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies. Bioorg Med Chem. 2014 Oct 1;22(19):5279-89. doi: 10.1016/j.bmc.2014.08.002. Epub 2014 Aug 12. PubMed PMID: 25172148; PubMed Central PMCID: PMC4172545. 12: Loranger MW, Forget SM, McCormick NE, Syvitski RT, Jakeman DL. Synthesis and evaluation of l-rhamnose 1C-phosphonates as nucleotidylyltransferase inhibitors. J Org Chem. 2013 Oct 4;78(19):9822-33. doi: 10.1021/jo401542s. Epub 2013 Sep 10. PubMed PMID: 24020932. 13: Sloothaak J, Odoni DI, Martins Dos Santos VA, Schaap PJ, Tamayo-Ramos JA. Identification of a Novel L-rhamnose Uptake Transporter in the Filamentous Fungus Aspergillus niger. PLoS Genet. 2016 Dec 16;12(12):e1006468. doi: 10.1371/journal.pgen.1006468. eCollection 2016 Dec. PubMed PMID: 27984587; PubMed Central PMCID: PMC5161314. 14: O'Neill EC, Stevenson CE, Paterson MJ, Rejzek M, Chauvin AL, Lawson DM, Field RA. Crystal structure of a novel two domain GH78 family α-rhamnosidase from Klebsiella oxytoca with rhamnose bound. Proteins. 2015 Sep;83(9):1742-9. doi: 10.1002/prot.24807. Epub 2015 Aug 6. PubMed PMID: 25846411; PubMed Central PMCID: PMC4690510. 15: Kim SM, Paek KH, Lee SB. Characterization of NADP+-specific L-rhamnose dehydrogenase from the thermoacidophilic Archaeon Thermoplasma acidophilum. Extremophiles. 2012 May;16(3):447-54. doi: 10.1007/s00792-012-0444-1. Epub 2012 Apr 6. PubMed PMID: 22481639. 16: Yin S, Liu M, Kong JQ. Functional analyses of OcRhS1 and OcUER1 involved in UDP-L-rhamnose biosynthesis in Ornithogalum caudatum. Plant Physiol Biochem. 2016 Dec;109:536-548. doi: 10.1016/j.plaphy.2016.10.029. Epub 2016 Nov 2. PubMed PMID: 27835851. 17: Paolini A, Guarch CP, Ramos-López D, de Lapuente J, Lascialfari A, Guari Y, Larionova J, Long J, Nano R. Rhamnose-coated superparamagnetic iron-oxide nanoparticles: an evaluation of their in vitro cytotoxicity, genotoxicity and carcinogenicity. J Appl Toxicol. 2016 Apr;36(4):510-20. doi: 10.1002/jat.3273. Epub 2015 Dec 28. PubMed PMID: 26708321. 18: Aalbergsjø SG, Sagstuen E. New Evidence for Hydroxyalkyl Radicals and Light- and Thermally Induced Trapped Electron Reactions in Rhamnose. Radiat Res. 2015 Aug;184(2):161-74. Epub 2015 Jul 24. PubMed PMID: 26207688. 19: Sarkar S, Salyer AC, Wall KA, Sucheck SJ. Synthesis and immunological evaluation of a MUC1 glycopeptide incorporated into l-rhamnose displaying liposomes. Bioconjug Chem. 2013 Mar 20;24(3):363-75. doi: 10.1021/bc300422a. Epub 2013 Mar 8. PubMed PMID: 23444835; PubMed Central PMCID: PMC3623543. 20: Li X, Rao X, Cai L, Liu X, Wang H, Wu W, Zhu C, Chen M, Wang PG, Yi W. Targeting Tumor Cells by Natural Anti-Carbohydrate Antibodies Using Rhamnose-Functionalized Liposomes. ACS Chem Biol. 2016 May 20;11(5):1205-9. doi: 10.1021/acschembio.6b00173. Epub 2016 Mar 18. PubMed PMID: 26982552.