Totomycin

Totomycin

Systematic (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
Identifiers
CAS Number	6379-56-2
ATC code	none
PubChem	CID 6433481
ChemSpider	4938630
Synonyms	Hygromycin A, Homomycin
Chemical data
Formula	C23H29NO12
Molar mass	511.475 g/mol
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 Key:YQYJSBFKSSDGFO-IIHALWDASA-N
Physical data
Melting point	110 to 112 °C (230 to 234 °F) (decomp.)
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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

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