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CAS 7205-49-4

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D-Streptamine, O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-, sulfate (1:1)

Description:
D-Streptamine is a complex aminoglycoside antibiotic characterized by its unique structural features, including multiple sugar moieties and amino groups. It is derived from Streptomyces griseus and plays a crucial role in inhibiting bacterial protein synthesis by binding to the 30S ribosomal subunit. The compound's structure includes a β-L-idopyranosyl unit linked to a β-D-ribofuranosyl unit, which is further connected to a 2-amino-2-deoxy-α-D-glucopyranosyl unit. This intricate arrangement contributes to its biological activity and solubility properties. D-Streptamine is typically used in the treatment of various bacterial infections, particularly those caused by Gram-negative bacteria. Its sulfate form enhances its stability and solubility in aqueous solutions, making it suitable for pharmaceutical applications. However, like other aminoglycosides, it may exhibit nephrotoxicity and ototoxicity, necessitating careful monitoring during therapeutic use. Overall, D-Streptamine's structural complexity and mechanism of action underscore its significance in antibiotic therapy.
Formula:C23H45N5O14·H2O4S
InChI:InChI=1S/C23H45N5O14.H2O4S/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1
InChI key:InChIKey=LJRDOKAZOAKLDU-UDXJMMFXSA-N
SMILES:S(=O)(=O)(O)O.O([C@H]1[C@H](O[C@H]2[C@H](O)[C@H](O[C@H]3O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H](CO)O2)[C@@H](O)[C@H](N)C[C@@H]1N)[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4N
Synonyms:
  • Paromomycin, sulfate (1:1)
  • D-Streptamine, O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)-O-[2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy-, sulfate (1:1)
  • Hydroxymycin, sulfate
  • D-Streptamine, O-2-amino-2-deoxy-α-D-glucopyranosyl-(1→4)-O-[O-2,6-diamino-2,6-dideoxy-β-L-idopyranosyl-(1→3)-O-β-D-ribofuranosyl-(1→5)]-2-deoxy-, sulfate (1:1) (salt)
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