Turanose: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
m r2.7.1) (Robot: Adding fa:تورانوس
No edit summary
 
(12 intermediate revisions by 12 users not shown)
Line 1: Line 1:
{{chembox
{{chembox
| Verifiedfields = changed
⚫
| verifiedrevid = 426915255
| Watchedfields = changed
|Name = <small>D</small>-Turanose
⚫
| verifiedrevid = 426915255
⚫
|ImageFile=Turanose.png
| Name = {{sm|d}}-Turanose
⚫
|ImageSize=200px
⚫
| ImageFile = Turanose.png
⚫
|IUPACName=(3''S'',4''R'',5''R'')-1,4,5,6-tetrahydroxy-3-[(2''R'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one
⚫
| ImageSize = 200px
|OtherNames=α-D-glucopyranosyl-(1→3)-α-D-fructopyranose
| IUPACName = α-<small>D</small>-glucopyranosyl-(1→3)-α-<small>D</small>-fructofuranose
⚫
|Reference=<ref>[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5460935 Turanose - Compound Summary], [[PubChem]]</ref>
| OtherNames =
⚫
|Section1={{Chembox Identifiers
⚫
| Reference = <ref>[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5460935 Turanose - Compound Summary], [[PubChem]]</ref>
⚫
| CASNo_Ref = {{cascite|correct|??}}
⚫
| SystematicName = (3''S'',4''R'',5''R'')-1,4,5,6-tetrahydroxy-3-[(2''R'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one
⚫
| Section1 = {{Chembox Identifiers
⚫
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=547-25-1
| CASNo=547-25-1
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| PubChem=5460935
| UNII = 6D600ARY3R
⚫
| SMILES=C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]([C@@H]([C@@H](CO)O)O)C(=O)CO)O)O)O)O
⚫
| PubChem = 5460935
⚫
| MeSHName=turanose
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4574343
⚫
| SMILES = O=C([C@@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@H](O)[C@H](O)CO)CO
| InChI = 1/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1
| InChIKey = RULSWEULPANCDV-PIXUTMIVBJ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RULSWEULPANCDV-PIXUTMIVSA-N
⚫
| MeSHName=turanose
}}
}}
|Section2={{Chembox Properties
| Section2 = {{Chembox Properties
| Formula=C<sub>12</sub>H<sub>22</sub>O<sub>11</sub>
| Formula=C<sub>12</sub>H<sub>22</sub>O<sub>11</sub>
| MolarMass=342.30 g/mol
| MolarMass=342.30 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
| Section3 = {{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}


'''Turanose''' is a [[Redox|reducing]] [[disaccharide]]. The <small>D</small>-isomer is naturally occurring. Its systematic name is α-<small>D</small>-glucopyranosyl-(1→3)-α-D-fructofuranose. It is an analog of [[sucrose]] not [[Metabolism|metabolized]] by [[Vascular plant|higher plants]], but rather acquired through the action of sucrose transporters for intracellular [[carbohydrate]] signaling. In addition to its involvement in signal transduction, <small>D</small>-(+)-turanose can also be used as a carbon source by many organisms including numerous species of [[bacteria]] and [[fungus|fungi]].<ref>{{cite journal | author = Sinha, A.K., et al. | title = Metabolizable and non-metabolizable sugars activate different signal transduction pathways in tomato | journal = Plant Physiol | volume = 128 | pages = 1480–1489 | year = 2002 | doi = 10.1104/pp.010771 | pmid = 11950996 | issue = 4 | pmc = 154275}}</ref><ref>{{cite journal | author = Gonzali, S., et al. | title = A turanose-insensitive mutant suggests a role for WOX5 in auxin homeostasis in Arabidopsis thaliana | journal = Plant J | volume = 44 | pages = 633–645 | year = 2005 | doi = 10.1111/j.1365-313X.2005.02555.x | pmid = 16262712 | issue = 4}}</ref><ref>{{cite journal | author = Sivitz, A.B., et al. | title = Arabidopsis sucrose transporter AtSUC9. High-affinity transport activity, intragenic control of expression, and early flowering mutant phenotype | journal = Plant Physiol | volume = 143 | pages = 188–198 | year = 2007 | doi = 10.1104/pp.106.089003 | pmid = 17098854 | issue = 1 | pmc = 1761979}}</ref><ref>{{cite journal | author = Loreti, E., et al. | title = Glucose and disaccharide-sensing mechanisms modulate the expression of α-amylase in barley embryos | journal = Plant Physiol | volume = 123 | pages = 939–948 | year = 2000 | doi = 10.1104/pp.123.3.939 | pmid = 10889242 | issue = 3 | pmc = 59056}}</ref><ref> [http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T2754 D-Turanose] at [[Sigma-Aldrich]]</ref>
'''Turanose''' is a [[Redox|reducing]] [[disaccharide]]. The {{sm|d}}-isomer is naturally occurring. Its systematic name is α-{{sm|d}}-glucopyranosyl-(1→3)-α-{{sm|d}}-fructofuranose. It is an analog of [[sucrose]] not [[Metabolism|metabolized]] by [[Vascular plant|higher plants]], but rather acquired through the action of sucrose transporters for intracellular [[carbohydrate]] signaling. In addition to its involvement in signal transduction, {{sm|d}}-(+)-turanose can also be used as a carbon source by many organisms including numerous species of [[bacteria]] and [[fungus|fungi]].<ref>{{cite journal | author = Sinha, A.K.| title = Metabolizable and non-metabolizable sugars activate different signal transduction pathways in tomato | journal = Plant Physiol | volume = 128 | pages = 1480–1489 | year = 2002 | doi = 10.1104/pp.010771 | pmid = 11950996 | issue = 4 | pmc = 154275|display-authors=etal}}</ref><ref>{{cite journal | author = Gonzali, S.| title = A turanose-insensitive mutant suggests a role for WOX5 in auxin homeostasis in Arabidopsis thaliana | journal = Plant J | volume = 44 | pages = 633–645 | year = 2005 | doi = 10.1111/j.1365-313X.2005.02555.x | pmid = 16262712 | issue = 4|display-authors=etal| doi-access = free }}</ref><ref>{{cite journal | author = Sivitz, A.B.| title = Arabidopsis sucrose transporter AtSUC9. High-affinity transport activity, intragenic control of expression, and early flowering mutant phenotype | journal = Plant Physiol | volume = 143 | pages = 188–198 | year = 2007 | doi = 10.1104/pp.106.089003 | pmid = 17098854 | issue = 1 | pmc = 1761979|display-authors=etal}}</ref><ref>{{cite journal | author = Loreti, E.| title = Glucose and disaccharide-sensing mechanisms modulate the expression of α-amylase in barley embryos | journal = Plant Physiol | volume = 123 | pages = 939–948 | year = 2000 | doi = 10.1104/pp.123.3.939 | pmid = 10889242 | issue = 3 | pmc = 59056|display-authors=etal}}</ref><ref> [http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T2754 D-Turanose] at [[Sigma-Aldrich]]</ref>


==References==
==References==
Line 38: Line 51:


[[Category:Disaccharides]]
[[Category:Disaccharides]]

[[ca:Turanosa]]
[[es:Turanosa]]
[[fa:تورانوس]]
[[fr:Turanose]]
[[gl:Turanosa]]
[[ja:ツラノース]]

Latest revision as of 15:27, 17 June 2023

d-Turanose[1]
Names
IUPAC name
α-D-glucopyranosyl-(1→3)-α-D-fructofuranose
Systematic IUPAC name
(3S,4R,5R)-1,4,5,6-tetrahydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.108 Edit this at Wikidata
MeSH turanose
UNII
  • InChI=1S/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1 ☒N
    Key: RULSWEULPANCDV-PIXUTMIVSA-N ☒N
  • InChI=1/C12H22O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4,6-16,18-21H,1-3H2/t4-,6-,7-,8-,9+,10-,11-,12-/m1/s1
    Key: RULSWEULPANCDV-PIXUTMIVBJ
  • O=C([C@@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@H](O)[C@H](O)CO)CO
Properties
C12H22O11
Molar mass 342.30 g/mol
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 ?)

Turanose is a reducing disaccharide. The d-isomer is naturally occurring. Its systematic name is α-d-glucopyranosyl-(1→3)-α-d-fructofuranose. It is an analog of sucrose not metabolized by higher plants, but rather acquired through the action of sucrose transporters for intracellular carbohydrate signaling. In addition to its involvement in signal transduction, d-(+)-turanose can also be used as a carbon source by many organisms including numerous species of bacteria and fungi.[2][3][4][5][6]

References[edit]

  1. ^ Turanose - Compound Summary, PubChem
  2. ^ Sinha, A.K.; et al. (2002). "Metabolizable and non-metabolizable sugars activate different signal transduction pathways in tomato". Plant Physiol. 128 (4): 1480–1489. doi:10.1104/pp.010771. PMC 154275. PMID 11950996.
  3. ^ Gonzali, S.; et al. (2005). "A turanose-insensitive mutant suggests a role for WOX5 in auxin homeostasis in Arabidopsis thaliana". Plant J. 44 (4): 633–645. doi:10.1111/j.1365-313X.2005.02555.x. PMID 16262712.
  4. ^ Sivitz, A.B.; et al. (2007). "Arabidopsis sucrose transporter AtSUC9. High-affinity transport activity, intragenic control of expression, and early flowering mutant phenotype". Plant Physiol. 143 (1): 188–198. doi:10.1104/pp.106.089003. PMC 1761979. PMID 17098854.
  5. ^ Loreti, E.; et al. (2000). "Glucose and disaccharide-sensing mechanisms modulate the expression of α-amylase in barley embryos". Plant Physiol. 123 (3): 939–948. doi:10.1104/pp.123.3.939. PMC 59056. PMID 10889242.
  6. ^ D-Turanose at Sigma-Aldrich
Retrieved from "https://en.wikipedia.org/w/index.php?title=Turanose&oldid=1160596357"