Table 1

1H NMR data for BPD 7- and 8-glucuronidesa

Peak 1Peak 2
ProtonBPDBPD-7S-GlucBPD-7R-GlucBPD-8S-Gluc
δ(ppm)
18.20,b dc8.19, m8.19, m8.19, m
28.00, t, J1,2 = J2,3 = 7.67.98, t, J1,2 = J2,3 = 7.67.99, m7.99, m
38.18,b d8.19, m8.19, m8.19, m
48.42, d8.06, d, J4,5 = 8.98.10, m8.10, m
58.42, d8.19, m8.10, m8.10, m
68.09, s8.79, s8.76, s8.48, s
75.08, d, J7,8 = 10.85.40, d, J7,8 = 10.15.35, d, J7,8 = 10.85.31, d, J7,8 = 9.7
84.58, ddd, J7,8 = 10.1; J8,9 = 2.5; J8,10 = 2.1∼4.87d∼4.8d∼4.8d
96.29, dd, J9,10 = 10.1; J8,9 = 2.56.27, dd, J9,10 = 10.1; J8,9 = 2.36.27, dd, J9,10 = 10.1; J8,9 = 2.56.58, dd, J9,10 = 10.1; J8,9 = 2.2
107.56, dd, J9,10 = 10.1; J8,10 = 2.17.55, dd, J9,10 = 10.3; J8,10 = 2.37.56, m7.56, m
118.42, d, J11,12 = 9.38.41, d, J10,11 = 9.48.42, d, J10,11 = 9.38.43, d, J10,11 = 9.4
128.13, d8.12, d, J11,12 = 9.38.10, m8.10, m
1′4.94, d, J1′,2′ = 7.34.75, d, J1′,2′ = 7.34.70, d, J1′,2′ = 7.7
  • a Recorded in methanol-d4.

  • b The assignment may be reversed.

  • c Abbreviations for coupling patterns: s, singlet; d, doublet; t, triplet; m, multiplet.

  • d Obscured by the residual methanol resonance; identified by two-dimensional COSY.