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)

* alpha-Galactosyl: Interactive image
* beta-Glucosyl: Interactive image

PubChem CID

* alpha-Galactosyl: 136693563
* beta-Glucosyl: 136594507

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/s1

Key: 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/s1

Key: CDYGCPPQERMCPE-DTYGZFTESA-N

SMILES

* alpha-Galactosyl: C1=CC(=CC=C1NN=C2C(=C(C(=O)C(=NNC3=CC=C(C=C3)O[C@@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)C2=O)N=NC5=CC=C(C=C5)O[C@@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O)O)O[C@@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O

* beta-Glucosyl: C1=CC(=CC=C1NN=C2C(=C(C(=O)C(=NNC3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C2=O)N=NC5=CC=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O

Properties

Chemical formula

| C42H48N6O21
Molar mass | 972.867 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

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.[1][2][3] It can therefore be used in their detection, quantification, precipitation, isolation, staining, and interfere with their function.[3][4] It was initially synthesised in 1962 as an antigen for carbohydrate-binding antibodies but has subsequently become more broadly used.[1][5] There are many variants of Yariv reagents which vary in the glycosyl groups on the outside of the structure, typically glucose, galactose, and mannose.[6]

A biographical article about Joseph Yariv was published by the Journal of Applied Crystallography. [7]

## References

1. ↑ 1.0 1.1 , Wikidata Q30798155
2. ↑ , Wikidata Q33531883
3. ↑ 3.0 3.1 , Wikidata Q38318749
4. ↑ , Wikidata Q74315380
5. ↑ , Wikidata Q42554063
6. ↑ "Yariv reagents for detection and quantitation of arabinogalactan-proteins". Biosupplies Australia. http://biosupplies.com.au/assets/files/docs/100-2_3_4_5_6_8.pdf.
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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*[CID]: Compound ID