Totomycin

Totomycin
Clinical data

ATC code	none
Identifiers
IUPAC name (E)-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-Trihydroxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]-3-[4-[(2S,3S,4S,5S)-5-acetyl-3,4-dihydroxyoxolan-2-yl]oxy-3-hydroxyphenyl]-2-methylprop-2-enamide
Synonyms	Hygromycin A, Homomycin
CAS Number	6379-56-2^Y
PubChem (CID)	6433481
ChemSpider	4938630^Y
Chemical and physical data
Formula	C₂₃H₂₉NO₁₂
Molar mass	511.475 g/mol
3D model (Jmol)	Interactive image
Melting point	110 to 112 °C (230 to 234 °F) (decomp.)
SMILES C/C(=C\C1=CC(=C(C=C1)O[C@H]2[C@H]([C@@H]([C@H](O2)C(=O)C)O)O)O)/C(=O)N[C@@H]3[C@@H]([C@H]([C@@H]4[C@H]([C@@H]3O)OCO4)O)O
InChI InChI=1S/C23H29NO12/c1-8(22(32)24-13-14(27)16(29)21-20(15(13)28)33-7-34-21)5-10-3-4-12(11(26)6-10)35-23-18(31)17(30)19(36-23)9(2)25/h3-6,13-21,23,26-31H,7H2,1-2H3,(H,24,32)/b8-5+/t13-,14+,15-,16-,17+,18+,19-,20+,21-,23-/m1/s1^Y Key:YQYJSBFKSSDGFO-IIHALWDASA-N^Y
^NY (what is this?) (verify)

Totomycin (also known as hygromycin A) is an aminoglycoside antibiotic produced by Streptomyces hygroscopicus, first described in the 1950s. The bacteria source is similar to that of hygromycin B from which the name of the compound was derived.

History

Hygromycin A was discovered in a soil sample from a forest near Indianapolis, Indiana in 1953 by Waksman and Henrici.^[1] Identification and structure of totomycin wasn't determined until 1957.

Antibiotic activity

The strongest antibiotic activity of totomycin is against Staphylococcus haemolyticus in which growth was inhibited by concentrations of 2 µg/mL. Other gram-positive and gram-negative sensitive to totomycin are inhibited by concentrations from 16 to 31 µg/mL.^[2]

Total synthesis

Totomycin has been a successful target in total synthesis since 1989.^[3]

References

↑ R.L. Mann et al., Antibiot. Chemother. 3, 1279 (1953)
↑ A new antibiotic, Totomycin. Brit. Pat., 758276 (1956)
↑ N. Chida et al., Chem. Commun. 1989, 436.

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