Table 2.
Properties of fully deprotected PS dinucleotide diastereomers
Rp a | Sp b | ||||||||
---|---|---|---|---|---|---|---|---|---|
Dimer | HRMS calc. | HRMS found | 31P NMRe | SVPDf | PDIIg | HRMS found | 31P NMRe | SVPDf | PDIIg |
usu | 617.09c | 617.09c | 56.74 | deg. | - | 617.09c | 55.55 | no deg. | - |
usUf | 605.07c | 605.07c | 56.78 | deg. | - | 605.07c | 55.68 | no deg. | - |
Ufsu | 605.07c | 605.07c | 56.82 | deg. | no deg. | 605.07c | 55.97 | no deg. | deg. |
asa | 641.17d | 641.17d | 57.51 | deg. | no deg. | 641.17d | 56.27 | no deg. | deg. |
Afsa | 629.15d | 629.15d | 57.21 | deg. | no deg. | 629.15d | 55.40 | no deg. | deg. |
asUf | 606.12d | 606.12d | 57.83 | deg. | no deg. | 606.12d | 56.63 | no deg. | deg. |
gsa | 657.16d | 657.16d | 56.07 | no deg. | deg. | 657.16d | 57.53 | deg. | no deg. |
aThe Rp diastereomer was the top spot on TLC for all dinucleotides except for gsa.
bThe Sp diastereomer was the lower spot on TLC for all dinucleotides except gsa.
cHRMS, high-resolution mass spectrometry: (M+Na).
dHRMS: (M+H).
eChemical shift (ppm) in 31P NMR spectrum of fully deprotected dinucleotide in D2O.
fSVPD degradation at 48 h time point.
gPDII degradation at 48 h time point. deg. indicates that there was degradation; no deg. indicates no degradation.
Lowercase u, a, and g indicate 2′-OMe nucleosides, lowercase s indicates PS linkage, and Uf and Af indicate 2′-F U and A nucleosides, respectively.