D-Lyxono-1,4-lactone
D-Lyxono-1,4-lactone is an inhibitor of the enzyme fucosidase. It competitively inhibits the enzyme, but does not inhibit other hydroxamic acids such as enantiomers of D-lyxono-1,4-lactone. D-Lyxono-1,4-lactone has been used to treat HIV and AIDS because it prevents viral replication by blocking the synthesis of glycoproteins in the virus’s envelope. It also has inhibitory effects on tumor cells that are not dependent on fucosidase activity. Magnetic resonance spectroscopy (NMR) studies have shown that d-lyxono-1,4-lactone binds to human liver cells and blocks the binding site for cytotoxic molecules in these cells.
D-lyxono-1,4-lactone is an aldonolactone obtained by cyclocondensation of the carboxy group and the 4-hydroxy group of D-lyxonic acid. It has a role as a plant metabolite. It derives from a D-lyxonic acid.
CAS Number |
15384-34-6 |
Product Name |
d-Lyxono-1,4-lactone |
IUPAC Name |
(3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one |
Molecular Formula |
C?H?O? |
Molecular Weight |
148.11 |
InChI |
InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3+,4+/m1/s1 |
SMILES |
C(C1C(C(C(=O)O1)O)O)O |
Synonyms |
D-Lyxonic Acid ?-Lactone; |
CAS No: 15384-34-6
MDL No: MFCD00270021
Chemical Formula: C5H8O5
Molecular Weight: 148.11 |
References:
1. Petasis NA, et al., Tetrahydron Asymmetry 1994, Vol5, No12, p2535-2562 |