| Revision as of 12:48, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 461284880 of page Rhamnose for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 16:17, 6 June 2024 edit CatboyQ (talk | contribs)20 editsm Fixed typo.Tags: Visual edit Mobile edit Mobile web edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 450951110 |
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| Watchedfields = changed |
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| verifiedrevid = 464381547 |
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| Reference = <ref>''Merck Index'', 11th Edition, '''8171'''.</ref> |
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| Reference = <ref>''Merck Index'', 11th Edition, '''8171'''.</ref> |
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| ImageFile = Alpha-L-Rhamnopyranose.svg |
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| ImageFile = Alpha-L-Rhamnopyranose.svg |
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| ImageSize = 100px |
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| ImageSize = 100px |
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| IUPACName = (''2R,3R,4R,5R,6S'')-6-methyloxane-2,3,4,5-tetrol |
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| IUPACName = 6-Deoxy-<small>L</small>-mannopyranose |
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| SystematicName = (2''R'',3''R'',4''R'',5''R'',6''S'')-6-Methyloxane-2,3,4,5-tetrol |
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| OtherNames = isodulcit<br>alpha-L-Rhamnose<br>L-rhamnose<br>L-mannomethylose<br>alpha-L-Rha<br>alpha-L-Rhamnoside<br>alpha-L-rhamnosides<br>alpha-L-Mannomethylose<br>6-deoxy-L-mannose |
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| OtherNames = Isodulcit<br>α-<small>L</small>-Rhamnose<br><small>L</small>-Rhamnose<br><small>L</small>-Mannomethylose<br>α-<small>L</small>-Rha<br>α-<small>L</small>-Rhamnoside<br>α-<small>L</small>-Mannomethylose<br>6-Deoxy-<small>L</small>-mannose<br><small>L</small>-Rhamnopyranose |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 18150 |
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| ChemSpiderID = 18150 |
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| InChI = 1/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 |
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| InChI = 1/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PNNNRSAQSRJVSB-BXKVDMCESA-N |
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| StdInChIKey = PNNNRSAQSRJVSB-BXKVDMCESA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 10485-94-6 --> |
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| CASNo = 3615-41-6 |
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| PubChem = 19233 |
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| PubChem = 19233 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01869 |
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| DrugBank = DB01869 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O=C(O)(O)(O)(O)C |
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| SMILES = O=C(O)(O)(O)(O)C |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6 | H=12 | O=5 |
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| Formula = C<sub>6</sub>H<sub>12</sub>O<sub>5</sub> |
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| Appearance = |
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| MolarMass = 164.16 g/mol |
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| ExactMass = 164.068473 |
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| Density = 1.41 g/mL |
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| MeltingPtC = 91 to 93 |
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| MeltingPt_notes = (monohydrate) |
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| MeltingPt = 91-93 °C (monohydrate) |
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| MagSus = -99.20·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section3 = {{Chembox Hazards |
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'''Rhamnose''' (Rha, Rham) is a naturally occurring ]. It can be classified as either a methyl-] or a 6-deoxy-]. Rhamnose predominantly occurs in nature in its ] as <small>L</small>-rhamnose (6-deoxy-<small>L</small>-]). This is unusual, since most of the naturally occurring sugars are in ]. Exceptions are the methyl pentoses <small>L</small>-] and <small>L</small>-rhamnose and the pentose <small>L</small>-]. However, examples of naturally-occurring <small>D</small>-rhamnose include some species of bacteria, such as '']'' and '']''.<ref>{{cite journal |vauthors=Melamed J, Kocev A, Torgov V, Veselovsky V, Brockhausen I | year = 2022 | title = Biosynthesis of the Pseudomonas aeruginosa common polysaccharide antigen by D‐Rhamnosyltransferases WbpX and WbpY | journal = Glycoconjugate Journal | doi = 10.1007/s10719-022-10040-4 | pmid = 35166992 | pmc = 8853325}}</ref> |
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Rhamnose can be isolated from ] (''Rhamnus''), ], and plants in the genus '']''. Rhamnose is also produced by ] belonging to class ].<ref>{{cite journal |author=Brown, M. R. |title=The amino-acid and sugar composition of 16 species of microalgae used in mariculture |year=1991 | journal = Journal of Experimental Marine Biology and Ecology |volume=145 |pages=79 |doi=10.1016/0022-0981(91)90007-J }}</ref> |
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Rhamnose is commonly bound to other sugars in nature. It is a common ] component of ]s from many plants. Rhamnose is also a component of the outer cell membrane of ] bacteria in the '']'' genus, which includes the organism that causes ].<ref>{{cite book |editor=Golan, David E. |others=Armen H. Tashjian Jr., Ehrin J. Armstrong, Joshua N. Galanter, April Wang Armstrong, Ramy A. Arnaout, Harris S. Rose |title=Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy |year=2005 |publisher=Lippincott Williams and Wilkins |isbn=0-7817-4678-7 |chapter=Chapter 35 - Pharmacology of the Bacterial Cell Wall |page=569 }}</ref> Natural antibodies against <small>L</small>-rhamnose are present in human serum,<ref>{{cite journal | vauthors = Oyelaran O, ], Dodd L, Gildersleeve JC | year = 2009 | title = Profiling Human Serum Antibodies with a Carbohydrate Antigen Microarray| doi = 10.1021/pr900515y | pmid = 19624168 | journal = J. Proteome Res.| volume = 8| issue = 9| pages = 4301–10| pmc = 2738755}}</ref> and the majority of people seem to possess ], ] or both of these types of ] capable of binding this ].<ref>{{cite journal | vauthors = Wang X, Chen H, Chiodo F, Tefsen B | year = 2019 | title = Detection of human IgM and IgG antibodies by means of galactofuranose-coated and rhamnose-coated gold nanoparticles| journal = Matters }} https://sciencematters.io/articles/201908000004 </ref> |
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An interesting particularity of rhamnose is the presence of ] production when reacted with ]s in the ] ] reaction, that makes it very useful to remove excess periodate in ] or other vicinal ] analysis, that would otherwise give colored blank issues.<ref>{{cite book |editor=Ashworth, M. R. F. |title=Analytical methods for glycerol |year=1979 |publisher=Academic Press |chapter=Chapter 3}}</ref> |
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==See also== |
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* ], despite the name, often binds rhamnose |
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* ] |
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Disaccharides: |
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* ], rhamnose-glucose |
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* ], rhamnose-glucose |
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* ], rhamnose-galactose |
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Polysaccharides: |
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* ] -glucose-]-glucose-rhamnose- |
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* ] |
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Glycosides: |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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<References/> |
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==Further reading== |
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* {{cite journal |doi=10.1099/0022-1317-28-1-29|pmid=239994|title=Use of L-rhamnose to Study Irreversible Adsorption of Bacteriophage PL-1 to a Strain of Lactobacillus casei|journal=Journal of General Virology|volume=28|issue=1|pages=29–35|year=1975|last1=Watanabe|first1=K|last2=Takesue|first2=S|doi-access=free}} |
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{{Carbohydrates}} |
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] |