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Yariv reagent

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Yariv reagent
Yariv reagent. Three example R groups shown: β-D-Galactose (βGal), β-D-Glucose (βGlc), β-D-Mannose (βMan).
Identifiers
3D model (JSmol)
PubChem CID
InChI
  • alpha-Galactosyl: InChI=1S/C42H48N6O21/c49-13-22-28(52)34(58)37(61)40(67-22)64-19-7-1-16(2-8-19)43-46-25-31(55)26(47-44-17-3-9-20(10-4-17)65-41-38(62)35(59)29(53)23(14-50)68-41)33(57)27(32(25)56)48-45-18-5-11-21(12-6-18)66-42-39(63)36(60)30(54)24(15-51)69-42/h1-12,22-24,28-30,34-44,49-54,56,58-63H,13-15H2/t22-,23-,24-,28+,29+,30+,34+,35+,36+,37-,38-,39-,40+,41+,42+/m1/s1Key: CDYGCPPQERMCPE-LKQUKSTNSA-N
  • beta-Glucosyl: InChI=1S/C42H48N6O21/c49-13-22-28(52)34(58)37(61)40(67-22)64-19-7-1-16(2-8-19)43-46-25-31(55)26(47-44-17-3-9-20(10-4-17)65-41-38(62)35(59)29(53)23(14-50)68-41)33(57)27(32(25)56)48-45-18-5-11-21(12-6-18)66-42-39(63)36(60)30(54)24(15-51)69-42/h1-12,22-24,28-30,34-44,49-54,56,58-63H,13-15H2/t22-,23-,24-,28-,29-,30-,34+,35+,36+,37-,38-,39-,40-,41-,42-/m1/s1Key: CDYGCPPQERMCPE-DTYGZFTESA-N
SMILES
  • alpha-Galactosyl: C1=CC(=CC=C1NN=C2C(=C(C(=O)C(=NNC3=CC=C(C=C3)O4((((O4)CO)O)O)O)C2=O)N=NC5=CC=C(C=C5)O6((((O6)CO)O)O)O)O)O7((((O7)CO)O)O)O
  • beta-Glucosyl: C1=CC(=CC=C1NN=C2C(=C(C(=O)C(=NNC3=CC=C(C=C3)O4((((O4)CO)O)O)O)C2=O)N=NC5=CC=C(C=C5)O6((((O6)CO)O)O)O)O)O7((((O7)CO)O)O)O
Properties
Chemical formula C42H48N6O21
Molar mass 972.867 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Yariv reagent (1,3,5-tri(p-glycosyloxyphenylazo)-2,4,6-trihydroxybenzene) is a glycosylated phenolic compound that binds strongly to galactans and arabinogalactan proteins. It can therefore be used in their detection, quantification, precipitation, isolation, staining, and interfere with their function. It was initially synthesised in 1962 as an antigen for carbohydrate-binding antibodies but has subsequently become more broadly used. There are many variants of Yariv reagents which vary in the glycosyl groups on the outside of the structure, typically glucose, galactose, and mannose.

A biographical article about Joseph Yariv was published by the Journal of Applied Crystallography.

References

  1. ^ B S Paulsen; David Craik; Dave E. Dunstan; B A Stone; A Bacic (20 January 2014). "The Yariv reagent: behaviour in different solvents and interaction with a gum arabic arabinogalactan-protein". Carbohydrate Polymers. 106: 460–468. doi:10.1016/J.CARBPOL.2014.01.009. ISSN 0144-8617. PMID 24721102. Wikidata Q30798155.
  2. Esther M Göllner; Wolfgang Blaschek; Birgit Classen (1 March 2010). "Structural investigations on arabinogalactan-protein from wheat, isolated with Yariv reagent". Journal of Agricultural and Food Chemistry. 58 (6): 3621–3626. doi:10.1021/JF903843F. ISSN 0021-8561. PMID 20163180. Wikidata Q33531883.
  3. ^ Kiminari Kitazawa; Theodora Tryfona; Yoshihisa Yoshimi; et al. (7 January 2013). "β-galactosyl Yariv reagent binds to the β-1,3-galactan of arabinogalactan proteins" (PDF). Plant Physiology. 161 (3): 1117–1126. doi:10.1104/PP.112.211722. ISSN 0032-0889. PMC 3585584. PMID 23296690. Wikidata Q38318749.
  4. A Chapman; A S Blervacq; J Vasseur; J L Hilbert (1 August 2000). "Arabinogalactan-proteins in Cichorium somatic embryogenesis: effect of beta-glucosyl Yariv reagent and epitope localisation during embryo development". Planta. 211 (3): 305–314. doi:10.1007/S004250000299. ISSN 0032-0935. PMID 10987548. Wikidata Q74315380.
  5. YARIV J; RAPPORT MM; GRAF L (1 November 1962). "The interaction of glycosides and saccharides with antibody to the corresponding phenylazo glycosides". Biochemical Journal. 85: 383–388. doi:10.1042/BJ0850383. ISSN 0264-6021. PMC 1243744. PMID 14002491. Wikidata Q42554063.
  6. "Yariv reagents for detection and quantitation of arabinogalactan-proteins" (PDF). Biosupplies Australia. Archived (PDF) from the original on 2021-01-16. Retrieved 2021-01-16.
  7. John R. Helliwell and Yariv family, "Joseph Yariv (1927–2021)", Journal of Applied Crystallography, Volume 54| Part 3| June 2021| Pages 1025-1026, doi:10.1107/S1600576721004453
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