Apiose

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Structural formula
Structural formula of D-apiose
General
Surname Apiose
other names
  • 3-C-hydroxymethyl- D -glycerotetrose ( D -apiose, open-chain form);
  • 3-C- (hydroxymethyl) - D -erythrofuranose ( D- apiose, ring shape)
  • 3-C- (hydroxymethyl) - L -threofuranose ( D- apiose, ring shape)
  • D -Apio- D -furanose (not clear)
  • L -Apio- D -furanose (not clear)
Molecular formula C 5 H 10 O 5
Brief description

colorless powder

External identifiers / databases
CAS number
  • 639-97-4 ( D -Apiose)
  • 6477-44-7 ( L apiosis)
  • 42927-70-8 ( DL apiosis)
Wikidata Q3276683
properties
Molar mass 150.13 g mol −1
Physical state

firmly

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Apiose (more precisely: D -Apiose) is a carbohydrate from plants . It occurs in higher concentrations in parsley and celery .

properties

Apiose is a branched sugar. It occurs in plants in pectins of the galacturonan type. It is a main component of the polysaccharides of the plant cell wall . It is also used in plants for the glycosylation of various secondary metabolites , e.g. B. QS-21 .

The apiose-1-reductase produces from D -apiitol and NAD + D -apiose, NADH and H + . The flavone apiosyltransferase uses UDP-apiose and 5,7,4'-trihydroxyflavone-7- O -beta- D -glucoside to generate UDP , 5,7,4'-trihydroxyflavone (synonym apigenin ) and 7- O -beta - D -Apiosyl- (1-> 2) -beta- D -glucoside.

literature

  • RR Watson, NS Orenstein: Chemistry and biochemistry of apiose. In: Advances in carbohydrate chemistry and biochemistry. Volume 31, 1975, pp. 135-184, PMID 775936 .

Individual evidence

  1. ↑ a b c d data sheet D-Apiose solution, ≥99.0% (HPLC) from Sigma-Aldrich , accessed on February 15, 2018 ( PDF ).
  2. ^ Zdzislaw E. Sikorski: Chemical and Functional Properties of Food Components, Third Edition. CRC Press, 2006, ISBN 978-1-420-00961-3 , p. 95.
  3. ↑ a b M. Pičmanová, BL Møller: apiose: one of nature's witty games. In: Glycobiology. Volume 26, Number 5, May 2016, pp. 430-442, doi : 10.1093 / glycob / cww012 , PMID 26848180