1,2,6-Trigalloylglucose

1,2,6-Trigalloylglucose
Chemical structure of 1,2,6-trigalloyl glucose
Chemical structure of 1,2,6-trigalloyl glucose
Names
IUPAC name
β-D-Glucopyranose 1,2,6-tris(3,4,5-trihydroxybenzoate)
Systematic IUPAC name
(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-{[(3,4,5-trihydroxybenzoyl)oxy]methyl}oxane-2,3-diyl bis(3,4,5-trihydroxybenzoate)
Other names
1,2,6-tris-O-galloyl-β-D-glucose
1-O,2-O,6-O-Trigalloyl-β-D-glucose
1,2,6-Tri-O-gallose-β-D-glucopyranose
1,2,6-Tris-O-(3,4,5-trihydroxybenzoyl)-β-D-glucopyranose
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C27H24O18/c28-11-1-8(2-12(29)19(11)36)18(35)23(40)25(45-27(43)10-5-15(32)21(38)16(33)6-10)24(41)22(39)17(34)7-44-26(42)9-3-13(30)20(37)14(31)4-9/h1-6,17,22,24-25,28-34,36-39,41H,7H2/t17-,22-,24+,25+/m1/s1 checkY=
    Key: XVILXNSBQKKWKL-UZLUZJFJSA-N checkY=
  • O[C@@H]1[C@@H](COC(C2=CC(O)=C(O)C(O)=C2)=O)O[C@@H](OC(C3=CC(O)=C(O)C(O)=C3)=O)[C@H](OC(C4=CC(O)=C(O)C(O)=C4)=O)[C@H]1O
Properties
C27H24O18
Molar mass 636.471 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2,6-Trigalloylglucose, or more specifically 1,2,6-tri-O-galloyl-β-D-glucose, is a gallotannin found in cell cultures of Cornus officinalis.[1]

Biosynthesis

The enzyme beta-glucogallin O-galloyltransferase, characterised from oak leaves, converts two units of glucogallin to 1,6-digalloylglucose:[2]

2
 
2D representation of the chemical structure of Glucogallin .
Glucogallin
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of 1,6-Digalloylglucose .
1,6-Digalloylglucose
+
 
2D representation of the chemical structure of Q23905964.
D-glucose

The product 1,6-digalloylglucose can react with another unit of glucogallin to give 1,2,6-trigalloylglucose.[3]

References

  1. ↑ Gallotannin production in cell cultures of Cornus officinalis Sieb. et Zucc. Yazaki K. and Okuda T., Plant cell reports, 1989, vol. 8, no6, pp. 346-349, INIST 7353523, doi:10.1007/BF00716670
  2. ↑ Gross, GG (1983). "Synthesis of mono-galloyl-beta-D-glucose di-galloyl-beta-D-glucose and trigalloyl-beta-D-glucose by beta-glucogallin-dependent galloyltransferases from oak leaves". Z. Naturforsch. C. 38: 519–523. doi:10.1515/znc-1983-7-804.
  3. ↑ Denzel K, Schilling G, Gross GG (1988). "Biosynthesis of gallotannins - enzymatic conversion of 1,6-digalloylglucose to 1,2,6-trigalloylglucose". Planta. 176 (1): 135–137. Bibcode:1988Plant.176..135D. doi:10.1007/BF00392489. PMID 24220744.
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