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| ImageFile1 = Fructose-asparagine-3D-balls.png
| ImageFile1 = Fructose-asparagine-3D-balls.png
| ImageSize1 = 200px
| ImageSize1 = 200px
| IUPACName = (2R)-4-amino-4-oxo-2-[[(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]butanoic acid
| IUPACName = (2R)-4-amino-4-oxo-2-[ [(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]butanoic acid
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
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| Function =
| Function =
| OtherCpds = }}
| OtherCpds = }}
}}
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'''Fructose-asparagine''' is a [[glycosylamine]] compound that is required for ''[[Salmonella]]'' to inflame the intestine.<ref>{{cite web|url=http://medicalxpress.com/news/2014-06-salmonella-achilles-heel-reliance-food.html|title=Salmonella's Achilles' heel: Reliance on single food source to stay potent|last=Caldwell|first=Emily|date=26 June 2014|publisher=Physorg|accessdate=26 June 2014}}</ref> The name of the genetic capability that encodes the uptake capability in ''Salmonella'' is ''fra''.<ref name="Tsolis2014">{{cite journal|last=Tsolis|first=Renée M.|coauthors=Mohamed M. Ali, David L. Newsom, Juan F. González, Anice Sabag-Daigle, Christopher Stahl, Brandi Steidley, Judith Dubena, Jessica L. Dyszel, Jenee N. Smith, Yakhya Dieye, Razvan Arsenescu, Prosper N. Boyaka, Steven Krakowka, Tony Romeo, Edward J. Behrman, Peter White, Brian M. M. Ahmer|year=2014|title=Fructose-Asparagine Is a Primary Nutrient during Growth of Salmonella in the Inflamed Intestine|journal=PLoS Pathogens|volume=10|issue=6|page=e1004209|issn=1553-7374|doi=10.1371/journal.ppat.1004209}}</ref> This ''fra'' has several genes: ''fraA'' (a regulator) ''fraB'' a fructose-asparagine deglycase, fraD a sugar kinase, ''fraA'' a fructose-asparagine transporter, and ''fra'' a L-asparaginase.<ref name="Tsolis2014"/>
'''Fructose-asparagine''' is a [[glycosylamine]] compound that is required for ''[[Salmonella]]'' to inflame the intestine.<ref>{{cite web|url=http://medicalxpress.com/news/2014-06-salmonella-achilles-heel-reliance-food.html|title=Salmonella's Achilles' heel: Reliance on single food source to stay potent|last=Caldwell|first=Emily|date=26 June 2014|publisher=Physorg|accessdate=26 June 2014}}</ref> The name of the genetic capability that encodes the uptake capability in ''Salmonella'' is ''fra''.<ref name="Tsolis2014">{{cite journal|last=Tsolis|first=Renée M.|coauthors=Mohamed M. Ali, David L. Newsom, Juan F. González, Anice Sabag-Daigle, Christopher Stahl, Brandi Steidley, Judith Dubena, Jessica L. Dyszel, Jenee N. Smith, Yakhya Dieye, Razvan Arsenescu, Prosper N. Boyaka, Steven Krakowka, Tony Romeo, Edward J. Behrman, Peter White, Brian M. M. Ahmer|year=2014|title=Fructose-Asparagine Is a Primary Nutrient during Growth of Salmonella in the Inflamed Intestine|journal=PLoS Pathogens|volume=10|issue=6|page=e1004209|issn=1553-7374|doi=10.1371/journal.ppat.1004209}}</ref> This ''fra'' has several genes: ''fraA'' (a regulator) ''fraB'' a fructose-asparagine deglycase, fraD a sugar kinase, ''fraA'' a fructose-asparagine transporter, and ''fra'' a L-asparaginase.<ref name="Tsolis2014"/>

Revision as of 12:40, 27 June 2014

Fructose-asparagine
File:Fructose-asparagine.svg
File:Fructose-asparagine-3D-balls.png
Names
IUPAC name
(2R)-4-amino-4-oxo-2-[ [(3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]butanoic acid
Identifiers
3D model (JSmol)
  • InChI=1S/C10H18N2O8/c11-6(14)1-4(9(17)18)12-3-10(19)8(16)7(15)5(13)2-20-10/h4-5,7-8,12-13,15-16,19H,1-3H2,(H2,11,14)(H,17,18)/t4-,5-,7-,8+,10?/m1/s1
    Key: AOBQWGHMIKNEHI-CWOUCCJVSA-N
  • C1C(C(C(C(O1)(CNC(CC(=O)N)C(=O)O)O)O)O)O
Properties
C10H18N2O8
Molar mass 294.25852
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

}} Fructose-asparagine is a glycosylamine compound that is required for Salmonella to inflame the intestine.[1] The name of the genetic capability that encodes the uptake capability in Salmonella is fra.[2] This fra has several genes: fraA (a regulator) fraB a fructose-asparagine deglycase, fraD a sugar kinase, fraA a fructose-asparagine transporter, and fra a L-asparaginase.[2]

Properties

Fructose-asparagine is a aminodeoxysugar. It takes the form of a pale yellow solid. It decomposes above 120°C.[3]

Production

Fructose-asparagine is formed when cooking food by way of the Maillard reaction. Fructose-asparagine can be prepared by refluxing D-glucose with sodium bisulfite in methanol, and then adding L-asparagine, and then acetic acid. An ion exchange resin then can separate the product from other contaminants.[3]

References

  1. ^ Caldwell, Emily (26 June 2014). "Salmonella's Achilles' heel: Reliance on single food source to stay potent". Physorg. Retrieved 26 June 2014.
  2. ^ a b Tsolis, Renée M. (2014). "Fructose-Asparagine Is a Primary Nutrient during Growth of Salmonella in the Inflamed Intestine". PLoS Pathogens. 10 (6): e1004209. doi:10.1371/journal.ppat.1004209. ISSN 1553-7374. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: unflagged free DOI (link)
  3. ^ a b "Material Data Sheet N-(1-Deoxy-D-fructos-1-yl)-L-asparagine" (PDF). Retrieved 27 June 2014.
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