RHAMNOSE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12O5
Molecular Weight	164.1567
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O

InChI

InChIKey=PNNNRSAQSRJVSB-BXKVDMCESA-N

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

HIDE SMILES / InChI

Description
Sources: https://doi.org/10.1016/0022-0981(91)90007-J | https://www.drugbank.ca/drugs/DB02961 | Golan, David E., ed. (2005). 'Chapter 35 - Pharmacology of the Bacterial Cell Wall'. Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Armen H. Tashjian Jr., Ehrin J. Armstrong, Joshua N. Galanter, April Wang Armstrong, Ramy A. Arnaout, Harris S. Rose. Lippincott Williams and Wilkins. p. 569. ISBN 0-7817-4678-7

Rhamnose is a naturally occurring deoxy sugar which can be classified as either a methyl-pentose or a 6-deoxy-hexose. Unlike most other naturally occurring sugars rhamnose is found in nature as L-rhamnose. Rhamnose can be isolated from plants such as Buckthorn, poison sumac, and those of the genus Uncaria. It is also produced by microalgae from class Bacillariophyceae. Throughout nature, rhamnose is commonly bound to other sugars. It is a common glycone component of glycosides in many plants. It also forms a component of the outer cell membrane in acid-fast bacteria of the genus Mycobaterium, including tuberculosis.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Enzymatic Synthesis of Rhamnose Containing Chemicals by Reverse Hydrolysis.	2015	26505759
Rhamnose glycoconjugates for the recruitment of endogenous anti-carbohydrate antibodies to tumor cells.	2014-07-07	24909955
L-rhamnose is often an important part of immunodominant epitope for pneumococcal serotype 23F polysaccharide antibodies in human sera immunized with PPV23.	2013	24391831
Molecular analysis of the genes involved in the biosynthesis of serotype specific polysaccharide in the novel serotype k strains of Streptococcus mutans.	2005-10	16101966
Purification, characterization, cDNA cloning, and expression of asialofetuin-binding C-type lectin from eggs of shishamo smelt (Osmerus [Spirinchus] lanceolatus).	2005-09-15	16112459
A simple method for the analysis of urinary sucralose for use in tests of intestinal permeability.	2005-05	15949159
Glutamine supplementation of parenteral nutrition does not improve intestinal permeability, nitrogen balance, or outcome in newborns and infants undergoing digestive-tract surgery: results from a double-blind, randomized, controlled trial.	2005-04	15798461
Lipopolysaccharide inner core oligosaccharide structure and outer membrane stability in human pathogens belonging to the Enterobacteriaceae.	2005	15949142
Platelet aggregation induced by serotype polysaccharides from Streptococcus mutans.	2004-05	15102769
Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine.	2002-09	12271438
Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level.	2001-12	11804209
Rapid and simultaneous quantification of rhamnose, mannitol, and lactulose in urine by HPLC for estimating intestinal permeability in pediatric practice.	1996-01	8565237
Use of Presumpto Plates to identify anaerobic bacteria.	1995-05	7615728
The effect of intestinal hypoperfusion on intestinal absorption and permeability during cardiopulmonary bypass.	1994-02	8299899
Glucose and citrate reduce the permeability changes caused by indomethacin in humans.	1992-05	1568563
Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species.	1990-10	2229345
Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes.	1987-12	2827574
The metabolism of L-rhamnose in animal tissues.	1965	5855461

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

L-RHAMNOSE

Preferred Name

English

RHAMNOSE

Official Name

English

RHAMNOSE [MI]

Common Name

English

L-(+)-RHAMNOSE

Common Name

English

NSC-2056

Code

English

NSC-287050

Code

English

L-RHAMNOSE [FHFI]

Common Name

English

Rhamnose [WHO-DD]

Common Name

English

(2R,3R,4S,5S)-2,3,4,5-TETRAHYDROXYHEXANAL

Systematic Name

English

(3R,4R,5R,6S)-6-METHYLTETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAOL

Systematic Name

English

FEMA NO. 3730

Code

English

RHAMNOSE, L-

Common Name

English

ISODULCIT

Common Name

English

RHAMNOSE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68484