Table 3.
Neoglycosides of natural products and small molecules.
| compound (type) |
neoglycosidea | natural form of glycosylation |
activity (parent) |
activity (neoglycoside) |
library size |
ref |
|---|---|---|---|---|---|---|
| betulinic acid (triterpenoid) |
8 X = O or NH
|
n/ab | apoptosis | anticancer or anti-HIV-1 | 32 (ester) 5 (amide) |
15 |
| calicheamicin (enediyne antibiotic) |
9 R = H or monosaccharide
|
aryltri- or tetrasaccharide | anticancer (DNA cleavage) | anticancer | 2 | 22 |
| chlorambucil (nitrogen mustard) |
10
|
n/a | anticancer (DNA alkylation) | anticancer | 63c | 16 |
| colchicine (alkaloid) |
11
|
n/a | tubulin polymeri- zation inhibitor | anticancer | 58 | 20 |
| cyclopamine (alkaloid) |
12
|
n/a | inhibition of Hedgehog pathway | anticancer | 16 (3R) 16 (3S) |
24 |
| digitoxin (steroid) |
13
|
tridigitoxoside | cardiac glycoside | anticancer | 39 (3R) 39(3S) |
19 |
| doxycycline (tetracycline) |
14
|
n/a | inhibition of bacterial protein synthesis | antibiotic | 37 | 26 |
| vancomycin (nonribosomal peptide) | 15 R = OH 16 R = N(OMe)sugar 
|
disaccharide | inhibition of bacterial cell wall synthesis | antibiotic | 8 (15) 8 (16) |
21 25 |
| warfarin (coumarin) |
17
|
n/a | anticoagulant | anticancer | 38 | 23 |
a
Saccharide depicted in red, handle in black, aglycon in blue.
b
Not naturally glycosylated.
c
Library consists of 54 neoglycosides attached by a methoxyamine handle, five by hydroxyamine, and four by hydrazide