Hygromycin B

Key facts

CAS number

31282-04-9

Purity

>90%

Form

Powder

form

Molecular weight

527.5 Da

Molecular formula

C₂₀H₃₇N₃O₁₃

PubChem

35766

Nature

Synthetic

Solubility

H₂O (~ 50 mg/ml)

Biochemical name

Hydromycin B

Biological description

An aminoglycoside antibiotic produced by Streptomyces hygroscopicus that is routinely used as a selection agent for cells that contain hph or hyg Hygromycin resistant gene. Hygromycin B is thought to inhibit protein synthesis by strengthening the interaction of peptidyl-tRNA in the ribosomal acceptor (“A”) site thereby preventing translocation of by EF-2 (elongation Factor-2). Hygromycin B is effective on most bacteria, fungi and higher eukaryotes.

Canonical smiles

CNC1CC(C(C(C1O)OC2C3C(C(C(O2)CO)O)OC4(O3)C(C(C(C(O4)C(CO)N)O)O)O)O)N

Isomeric smiles

CN[C@H]1C[C@H]([C@@H]([C@H]([C@@H]1O)O[C@H]2[C@@H]3[C@H]([C@H]([C@H](O2)CO)O)OC4(O3)[C@@H]([C@@H]([C@H]([C@H](O4)[C@H](CO)N)O)O)O)O)N

InChi

InChI=1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6+,7+,8-,9+,10-,11+,12-,13-,14-,15-,16+,17+,18-,19+,20?/m1/s1

InChiKey

GRRNUXAQVGOGFE-KPBUCVLVSA-N

IUPAC Name

(3'R,3aS,4S,4'R,5'R,6R,6'R,7S,7aS)-4-[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-[(1S)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol