Table 3 Analytical data of formed glycosides in the other five donor/acceptor combinations with purified MdP2′GT.

From: Purification and characterization of a novel phloretin-2′-O-glycosyltransferase favoring phloridzin biosynthesis

Donor/acceptor combinations

Glycosides

Rt (min)

m/z [M-H+]

NMR (500 MHz, DMSO-d6)

δ1H (ppm)

δ13C (ppm)

UDPG/Isoliquiritigenin

1

30.43

417.118

8.009 (1H, d, J = 8.8 Hz, H-6′), 7.837 (1H, d, J = 15.5 Hz, H-8), 7.806 (2H, d, J = 8.0, H-2,6), 7.720 (1H, d, J = 15.3 Hz, H-7), 7.182 (2H, d, J = 8.7 Hz, H-3,5), 6.438 (1H, dd, J = 2.0, 8.5 Hz, H-5′), 6.314 (1H, d, J = 2.0 Hz, H-3′), 5.011 (1H, d, J = 7.2 Hz, H-1″), 4.013 (1H, dd, J = 2.0, 11.8 Hz, H-6″), 3.745 (1H, dd, J = 5.3, 11.9 Hz, H-6″)

191.97 (C-9), 166.19 (C-4′), 165.16 (C-2′), 159.66 (C-4), 143.43 (C-8), 132.10 (C-6′), 130.02 (C-2,6), 129.13 (C-1), 118.65 (C-7), 116.60 (C-3,5), 113.28 (C-1′), 107.85 (C-5′), 102.43 (C-3′), 100.41 (C-1″), 76.86 (C-3″), 76.55 (C-5″), 73.44 (C-2″), 69.90 (C-4″), 61.07 (C-6″)

UDPG/Kaempferol

2

30.54

447.092

7.949 (2H, d, J = 9.0 Hz, H-2′, 6′), 6.798 (2H, d, J = 8.5 Hz, H-3′, 5′), 6.295 (1H, d, J = 2.0 Hz, H-8), 6.110 (1H, d, J = 2.0 Hz, H-6), 5.113 (1H, d, J = 7.0 Hz, H-1″), 3.088-3.573 (6H, m, sugar protons)

178.15 (C-4), 164.62 (C-7), 161.67 (C-5), 160.15 (C-4′), 157.81 (C-9), 157.14 (C-2), 134.18 (C-3), 130.87 (C-2′, 6′), 121.49 (C-1′), 114.71 (C-3′, 5′), 104.40 (C-10), 102.97 (C-1″), 98.58 (C-6), 93.43 (C-8), 76.97 (C-5″), 76.72 (C-3″), 74.38 (C-2″), 70.09 (C-4″), 61.37 (C-6″)

ADPG/Quercetin

3

28.81

463.087

7.502 (1H, dd, J = 7.5, 2.5 Hz, H-6′), 7.497 (1H, d, J = 2.4 Hz, H-2′), 6.774 (1H, d, J = 7.0 Hz, H-5′), 6.326 (1H, d, J = 2.1 Hz, H-8), 6.120 (1H, d, J = 2.0 Hz, H-6), 5.194 (1H, d, J = 7.4 Hz, H-1″)

177.97 (C-4), 164.46 (C-7), 161.49 (C-5), 157.09 (C-2), 156.89 (C-9), 148.46 (C-4′), 144.46 (C-3′), 134.15 (C-3), 121.60 (C-6′), 121.46 (C-1′), 116.35 (C-5′), 114.88 (C-2′), 104.20 (C-10), 103.40 (C-1″), 98.51 (C-6), 93.38 (C-8), 75.80 (C-5″), 73.55 (C-3″), 71.64 (C-2″), 68.48 (C-4″), 60.47 (C-6″)

UDP-Gal/Quercetin

4

28.75

463.091

7.491 (2H, dd, J = 7.8, 2.0 Hz, H-2′,6′), 6.773 (1H, d, J = 7.8 Hz, H-5′), 6.278 (1H, d, J = 2.0 Hz, H-8), 6.091 (1H, d, J = 2.0 Hz, H-6), 5.271 (1H, d, J = 7.3 Hz, H-1″), 3.706-3.285 (6H, m, sugar protons)

177.61 (C-4), 164.17 (C-7), 161.17 (C-5), 157.13 (C-2), 156.58 (C-9), 147.98 (C-4′), 144.03 (C-3′), 133.75 (C-3), 121.34 (C-6′), 121.20 (C-1′), 115.71 (C-5′), 114.13 (C-2′), 103.81 (C-10), 102.46 (C-1″), 98.03 (C-6), 92.85 (C-8), 76.52 (C-5″), 76.25 (C-3″), 73.87 (C-2″), 69.34 (C-4″), 60.68 (C-6″)

UDPG/Luteolin

5

27.60

447.092

7.41 (1H, d, J = 2.4 Hz, H-2′), 7.35 (1H, dd, J = 8.4, 2.4 Hz, H-6′), 6.89 (1H, d, J = 8.4 Hz, H-5′), 6.77 (1H, d, J = 2.4 Hz, H-8), 6.75 (1H, s, H-3), 6.43 (1H, d, J = 2.4 Hz, H-6), 5.07 (1H, d, J = 7.2 Hz, H-1″)

181.68 (C-4), 164.34 (C-2), 162.60 (C-7), 160.72 (C-5), 156.75 (C-9), 149.10 (C-4′), 145.05 (C-3′), 121.37 (C-1′), 118.53 (C-6′), 115.07 (C-2′), 112.50 (C-5′), 105.01 (C-10), 102.47 (C-3), 99.59 (C-6), 99.01 (C-1″), 94.10 (C-8), 76.47 (C-3″), 75.81 (C-5″), 72.68 (C-2″), 69.14 (C-4″), 60.29 (C-6″)

aUDPG/Phloretin

6

28.04

437.256

2.79 (2H, t, J = 7.4 Hz, H-7), 3.03 (2H, dd, J = 11.4 Hz, H-2″, 4″), 3.11 (1H, m, J = 5.1 Hz, H-5′′), 3.20 (1H, m, J = 4.7 Hz, H-3″), 3.38 (2H, m, J = 8.3 Hz, H-8), 3.62 (2H, dd, J = 5.4, 11.8 Hz, H-6″), 4.94 (1H, d, J = 6.8 Hz, H-1″), 5.86 (2H, d, J = 1.9 Hz, H-3, 5), 6.08 (1H, d, J = 1.8 Hz, H-3′), 6.59 (2H, d, J = 8.1 Hz, H-2, 6), 6.95 (1H, d, J = 8.4 Hz, H-5′)

29.43 (C-7), 45.56 (C-8), 61.02 (C-6″), 69.68 (C-4″), 73.30 (C-2″), 77.00 (C-5″), 77.08 (C-3″), 94.05 (C-5′), 96.96 (C-3′), 100.66 (C-1″), 105.37 (C-1′), 114.68 (C-2 and C-6), 128.99 (C-3 and C-5), 132.48 (C-1), 154.97 (C-4), 160.91 (C-4′), 164.58 (C-6′), 166.16 (C-2′), 205.14 (C-9)

aADPG/Phloretin

  1. aThe formed glycoside in UDPG/Phloretin and ADPG/Phloretin combinations was determined in our previous unpunished study and identified as phloridzin.
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