Fuculose

Last updated
l-Fuculose
L-Fuculose furanose chemical structure.png
L-Fuculose chemical structure.png
Names
IUPAC name
6-Deoxy-l-tagatose
Systematic IUPAC name
(3R,4S,5S)-2-(Hydroxymethyl)-5-methyltetrahydrofuran-2,3,4-triol
Identifiers
3D model (JSmol)
PubChem CID
  • O[C@H]1[C@@H](O)C(O)(CO)O[C@H]1C
Properties
C6H12O5
Molar mass 164.16 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fuculose or 6-deoxy-tagatose is a ketohexose deoxy sugar. [1] [2] Fuculose is involved in the process of sugar metabolism. [3] l-Fuculose can be formed from l-fucose by l-fucose isomerase and converted to L-fuculose-1-phosphate by l-fuculose kinase. [4]

See also

Related Research Articles

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A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 and thus with the empirical formula Cm(H2O)n, which does not mean the H has covalent bonds with O. However, not all carbohydrates conform to this precise stoichiometric definition, nor are all chemicals that do conform to this definition automatically classified as carbohydrates.

<span class="mw-page-title-main">Glucose</span> Naturally produced monosaccharide

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<span class="mw-page-title-main">Hexose</span> 6-Carbon simple sugar

In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.

<span class="mw-page-title-main">Mannose</span> Chemical compound

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Fucose is a hexose deoxy sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian, insect and plant cell surface. Fucose is the fundamental sub-unit of the seaweed polysaccharide fucoidan. The α(1→3) linked core of fucoidan is a suspected carbohydrate antigen for IgE-mediated allergy.

Rhamnose is a naturally occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose predominantly occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Exceptions are the methyl pentoses L-fucose and L-rhamnose and the pentose L-arabinose. However, examples of naturally-occurring D-rhamnose include some species of bacteria, such as Pseudomonas aeruginosa and Helicobacter pylori.

<span class="mw-page-title-main">Glycosyltransferase</span> Class of enzymes that catalyze the transfer of glycosyl groups to an acceptor

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<span class="mw-page-title-main">UTP—glucose-1-phosphate uridylyltransferase</span> Class of enzymes

UTP—glucose-1-phosphate uridylyltransferase also known as glucose-1-phosphate uridylyltransferase is an enzyme involved in carbohydrate metabolism. It synthesizes UDP-glucose from glucose-1-phosphate and UTP; i.e.,

dTDP-4-dehydrorhamnose 3,5-epimerase

In enzymology, a dTDP-4-dehydrorhamnose 3,5-epimerase is an enzyme that catalyzes the chemical reaction

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Ribose-5-phosphate isomerase (Rpi) encoded by the RPIA gene is an enzyme that catalyzes the conversion between ribose-5-phosphate (R5P) and ribulose-5-phosphate (Ru5P). It is a member of a larger class of isomerases which catalyze the interconversion of chemical isomers. It plays a vital role in biochemical metabolism in both the pentose phosphate pathway and the Calvin cycle. The systematic name of this enzyme class is D-ribose-5-phosphate aldose-ketose-isomerase.

<span class="mw-page-title-main">2-Dehydro-3-deoxy-phosphogluconate aldolase</span> Class of enzymes

The enzyme 2-dehydro-3-deoxy-phosphogluconate aldolase, commonly known as KDPG aldolase, catalyzes the chemical reaction

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<span class="mw-page-title-main">GDP-mannose 4,6-dehydratase</span>

The enzyme GDP-mannose 4,6-dehydratase (EC 4.2.1.47) catalyzes the chemical reaction

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Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H. The naturally-occurring form, d-ribose, is a component of the ribonucleotides from which RNA is built, and so this compound is necessary for coding, decoding, regulation and expression of genes. It has a structural analog, deoxyribose, which is a similarly essential component of DNA. l-ribose is an unnatural sugar that was first prepared by Emil Fischer and Oscar Piloty in 1891. It was not until 1909 that Phoebus Levene and Walter Jacobs recognised that d-ribose was a natural product, the enantiomer of Fischer and Piloty's product, and an essential component of nucleic acids. Fischer chose the name "ribose" as it is a partial rearrangement of the name of another sugar, arabinose, of which ribose is an epimer at the 2' carbon; both names also relate to gum arabic, from which arabinose was first isolated and from which they prepared l-ribose.

References

  1. Lindhorst TK (2007). Essentials of Carbohydrate Chemistry and Biochemistry (1 ed.). Wiley-VCH. ISBN   978-3-527-31528-4.
  2. Robyt JF (1997). Essentials of Carbohydrate Chemistry (1st ed.). Springer. ISBN   0-387-94951-8.
  3. Wen L, Zang L, Huang K, Li S, Wang R, Wang PG (February 2016). "Efficient enzymatic synthesis of L-rhamnulose and L-fuculose". Bioorganic & Medicinal Chemistry Letters. 26 (3): 969–972. doi:10.1016/j.bmcl.2015.12.051. PMC   5984655 . PMID   26778148.
  4. Iqbal, Muhammad Waheed; et al. (2021). "A review on selective l-fucose/d-arabinose isomerases for biocatalytic production of l-fuculose/d-ribulose". International Journal of Biological Macromolecules. 168: 558–571. doi:10.1016/j.ijbiomac.2020.12.021. PMID   33296692. S2CID   228088451.