Turanose: Difference between revisions

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
CAS Number	547-25-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	4574343 ;
ECHA InfoCard	100.008.108
MeSH	turanose
PubChem CID	5460935;
UNII	6D600ARY3R ;
CompTox Dashboard (EPA)	DTXSID90876998 ;
	InChI 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 Key: RULSWEULPANCDV-PIXUTMIVSA-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;
	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;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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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]

^ Turanose - Compound Summary, PubChem
^ 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.
^ 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.
^ 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.
^ 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.
^ D-Turanose at Sigma-Aldrich

[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

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@@ Line 1: / Line 1: @@
-{{chembox new
+{{chembox
+| Verifiedfields = changed
-|ImageFile=Turanose.svg
+| Watchedfields  = changed
-|ImageSize=
+| verifiedrevid  = 426915255
-|IUPACName=1,4,5,6-tetrahydroxy-3-[3,4,5-
+| Name           = {{sm|d}}-Turanose
-trihydroxy-6-(hydroxymethyl)oxan-
+| ImageFile      = Turanose.png
--yl]oxyhexan-2-one
+| ImageSize      = 200px
-|OtherNames=
+| 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=219660 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=547-25-1
+| 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
-|  PubChem=219660
+| Section1       = {{Chembox Identifiers
-|  SMILES=C(C1C(C(C(C(O1)OC(C(C(CO)O)O)C(=O)CO)O)O)O)O
+| CASNo_Ref = {{cascite|correct|??}}
-|  MeSHName=turanose
+| CASNo=547-25-1
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 6D600ARY3R
+| PubChem = 5460935
+| 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=342.29648
+| 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=
   }}
 }}
-D-(+)-'''Turanose''' is a [[Redox|reducing]] [[disaccharide]].  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, D-(+)-Turanose can also be used as a [[carbon]] source by many organisms including numerous species of [[bacteria]] and fungi.  <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>
-Sinha, A.K., et al., Metabolizable and non-metabolizable sugars activate different signal transduction pathways in tomato. Plant Physiol. 128, 1480-1489, (2002)</ref><ref>
-Gonzali, S., et al., A turanose-insensitive mutant suggests a role for WOX5 in auxin homeostasis in Arabidopsis thaliana. Plant J. 44, 633-645, (2005)</ref><ref>
-Sivitz, A.B., et al., Arabidopsis sucrose transporter AtSUC9. High-affinity transport activity, intragenic control of expression, and early flowering mutant phenotype. Plant Physiol. 143, 188-198, (2007)</ref><ref>
-Loreti, E., et al., Glucose and disaccharide-sensing mechanisms modulate the expression of α-amylase in barley embryos. Plant Physiol. 123, 939-948, (2000)</ref><ref>http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/T2754</ref>
 ==References==
 {{Reflist}}
+{{carbohydrates}}
-[[Category:Disaccharides]]
+[[Category:Disaccharides]]
-[[fr:Turanose]]