Totomycin

Totomycin
Clinical data
Other names	Hygromycin A, Homomycin
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;
CAS Number	6379-56-2 ;
PubChem CID	6433481;
ChemSpider	4938630 ;
UNII	3YJY415DDI;
Chemical and physical data
Formula	C23H29NO12
Molar mass	511.480 g·mol−1
3D model (JSmol)	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 ; Key:YQYJSBFKSSDGFO-IIHALWDASA-N ;
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Hygromycin A (also known as totomycin) is a modified cinnamic acid flanked by a furanose sugar and aminocyclitol (not to be confused with hygromycin B, belonging to an unrelated class of antibiotics, aminoglycosides). It is produced by Streptomyces hygroscopicus, first described in the 1950s.

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 was not determined until 1957.

Antibiotic activity

It was thought that the strongest antibiotic activity of totomycin was 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]

In 2021 it was reported that Hygromycin A is very effective against spirochetes and can be used to eliminate the spirochete that causes Lyme disease. Bait laced with hygromycin A could be used to eliminate Lyme disease in the wild.[3]

Total synthesis

Totomycin has been a successful target in total synthesis since 1989.[4]

References

Mann RL, Gale RM, Van Abelle FR (December 1953). "Hygromycin. II. Isolation and properties". Antibiotics & Chemotherapy. Northfield, Ill. 3 (12): 1279–82. PMID 24542809.
GB 758276, "A new antibiotic Totomycin.", issued 1956, assigned to Jacques Loewe Research Foundation.
Leimer N, Wu X, Imai Y, Morrissette M, Pitt N, Favre-Godal Q, et al. (October 2021). "A selective antibiotic for Lyme disease". Cell. 184 (21): 5405–5418.e16. doi:10.1016/j.cell.2021.09.011. PMC 8526400. PMID 34619078.
Chida N, Ohtsuka M, Nakazawa K, Ogawa S (1989). "Total synthesis of hygromycin A". Journal of the Chemical Society, Chemical Communications. 7 (7): 436–8. doi:10.1039/C39890000436.

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[pmid24542809-1] Mann RL, Gale RM, Van Abelle FR (December 1953). "Hygromycin. II. Isolation and properties". Antibiotics & Chemotherapy. Northfield, Ill. 3 (12): 1279–82. PMID 24542809.

[2] GB 758276, "A new antibiotic Totomycin.", issued 1956, assigned to Jacques Loewe Research Foundation.

[3] Leimer N, Wu X, Imai Y, Morrissette M, Pitt N, Favre-Godal Q, et al. (October 2021). "A selective antibiotic for Lyme disease". Cell. 184 (21): 5405–5418.e16. doi:10.1016/j.cell.2021.09.011. PMC 8526400. PMID 34619078.

[4] Chida N, Ohtsuka M, Nakazawa K, Ogawa S (1989). "Total synthesis of hygromycin A". Journal of the Chemical Society, Chemical Communications. 7 (7): 436–8. doi:10.1039/C39890000436.