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Sedoheptulose information


Sedoheptulose
Names
IUPAC name
D-altro-Hept-2-ulose[1]
Systematic IUPAC name
(3S,4R,5R,6R)-1,3,4,5,6,7-Hexahydroxyheptan-2-one
Other names
D-altro-2-Heptulose; D-altro-Heptulose
Identifiers
CAS Number
  • 3019-74-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16802 checkY
ChemSpider
  • 4573620 checkY
ECHA InfoCard 100.019.243 Edit this at Wikidata
MeSH Sedoheptulose
PubChem CID
  • 5459879
UNII
  • 40A0W1XJ6X checkY
CompTox Dashboard (EPA)
  • DTXSID10952581 Edit this at Wikidata
InChI
  • InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7-/m1/s1 checkY
    Key: HSNZZMHEPUFJNZ-SHUUEZRQSA-N checkY
  • InChI=1/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7-/m1/s1
    Key: HSNZZMHEPUFJNZ-SHUUEZRQBR
SMILES
  • O=C([C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO)CO
Properties
Chemical formula
C7H14O7
Molar mass 210.182 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Sedoheptulose or pseudoheptulose or D-altro-heptulose is a ketoheptose—a monosaccharide with seven carbon atoms and a ketone functional group. It is one of the few heptoses found in nature, and is found in various fruits and vegetables ranging from carrots and leeks to figs, mangos and avocados.[2][3]

It is an intermediate in respiratory and photosynthetic pathways and plays a vital role in the non-oxidative branch of the pentose phosphate pathway.[4][5]

Studies have shown that 7-O-galloyl-D-sedoheptulose, a chemical extracted from dogwood fruit, is able to reduce pro-inflammatory markers in vivo such as interleukin-6 (IL-6) and C-reactive protein and thus might be able reduce low-level inflammation in humans.[6] While this compound contains a sedoheptulose moiety, sedoheptulose itself has not been shown to possess the same properties.

  1. ^ "2-Carb-10". iupac.qmul.ac.uk. Retrieved 2023-11-14.
  2. ^ Ogata, James N.; Kawano, Yoshihiko; Bevenue, Arthur; Casarett, Louis J. (January 1972). "Ketoheptose content of some tropical fruits". Journal of Agricultural and Food Chemistry. 20 (1): 113–115. doi:10.1021/jf60179a011. PMID 5059931.
  3. ^ Okuda, Takuo; Mori, Kazuko (June 1974). "Distribution of manno-heptulose and sedoheptulose in plants". Phytochemistry. 13 (6): 961–964. Bibcode:1974PChem..13..961O. doi:10.1016/S0031-9422(00)91430-4.
  4. ^ Horecker, B. L; Smyrniotis, P. Z (1953). "Transaldolase: The Formation of Fructose-6-Phosphate from Sedoheptulose-7-Phosphate". Journal of the American Chemical Society. 75 (8): 2021. doi:10.1021/ja01104a532.
  5. ^ Patra, Krushna C; Hay, Nissim (2014). "The pentose phosphate pathway and cancer". Trends in Biochemical Sciences. 39 (8): 347–354. doi:10.1016/j.tibs.2014.06.005. PMC 4329227. PMID 25037503.
  6. ^ Park, Chan Hum; Tanaka, Takashi; Yokozawa, Takako (September 2013). "Evaluation of 7-O-galloyl-d-sedoheptulose, isolated from Corni Fructus, in the adipose tissue of type 2 diabetic db/db mice". Fitoterapia. 89: 131–142. doi:10.1016/j.fitote.2013.03.026. ISSN 0367-326X. PMID 23567861.

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Sedoheptulose

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Sedoheptulose or pseudoheptulose or D-altro-heptulose is a ketoheptose—a monosaccharide with seven carbon atoms and a ketone functional group. It is one...

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Calvin cycle

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2 fixation) are converted into sedoheptulose-1,7-bisphosphate (7C) by aldolase enzyme.[citation needed] Sedoheptulose-1,7-bisphosphatase (one of only...

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Transketolase

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fragment to a 5-carbon aldose (D-ribose-5-P) to form a 7-carbon ketose (sedoheptulose-7-P). The abstraction of two carbons from D-xylulose-5-P yields the...

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Heptose

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are few examples of seven-carbon sugars in nature, among which are: sedoheptulose or D-altro-heptulose (a ketose), an intermediate in the Calvin cycle...

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Transaldolase

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gene. The following chemical reaction is catalyzed by transaldolase: sedoheptulose 7-phosphate + glyceraldehyde 3-phosphate ⇌ {\displaystyle \rightleftharpoons...

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Sedoheptulokinase

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sedoheptulose ⇌ {\displaystyle \rightleftharpoons } ADP + sedoheptulose 7-phosphate Thus, the two substrates of this enzyme are ATP and sedoheptulose...

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Ketose

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ribulose, xylulose Hexoses: fructose, psicose, sorbose, tagatose Heptoses: sedoheptulose Octoses: D-manno-octulose (the basis for KDO) Nonoses: D-glycero-D-galacto-nonulose...

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Monosaccharide

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sugars. Examples of heptoses include the ketoses, mannoheptulose and sedoheptulose. Monosaccharides with eight or more carbons are rarely observed as they...

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Hylotelephium spectabile

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used as a laboratory plant where it is studied for its synthesis of sedoheptulose. Phytopurification and phytostabilisation of soils: the effects of heavy...

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Xanthan gum

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

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Dihydroxyacetone phosphate

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3-bisphosphoglycerate by NADPH. It is also used in the synthesis of sedoheptulose 1,7-bisphosphate and fructose 1,6-bisphosphate, both of which are used...

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Polysaccharide

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

Word Count : 3910

Sugar

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

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Pentose

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

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Chitin

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

Word Count : 2781

Carbohydrate

Last Update:

Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

Word Count : 5639

Starch

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

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Tetrose

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Phosphate Pathway, a transaldolase removes the first 3 carbon molecules of sedoheptulose 7-phosphate and places them onto a glyceraldehyde 3-phosphate. The transaldolase...

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Fructose

Last Update:

Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

Word Count : 5302

Pentose phosphate pathway

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ribose 5-phosphate → glyceraldehyde 3-phosphate + sedoheptulose 7-phosphate transketolase sedoheptulose 7-phosphate + glyceraldehyde 3-phosphate → erythrose...

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C7H14O7

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210.18 g/mol, exact mass: 210.0740 u) may refer to: Mannoheptulose Sedoheptulose, or D-altro-heptulose This set index page lists chemical structure articles...

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Cetoniacytone A

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proceed via the pentose phosphate pathway with sedoheptulose-7- phosphate as the key intermediate. Sedoheptulose-7- phosphate first undergoes a cyclization...

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Isomaltooligosaccharide

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

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Reducing sugar

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

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List of sugars

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Psicose Sorbose Tagatose Deoxy sugars Fucose Fuculose Rhamnose Heptoses Ketoheptoses Mannoheptulose Sedoheptulose Above 7 Octoses Nonoses Neuraminic acid...

Word Count : 901

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