Mycothiol

Mycothiol (MSH or AcCys-GlcN-Ins) is an unusual thiol compound found in the Actinomycetota.^[1][2] It is composed of a cysteine residue with an acetylated amino group linked to glucosamine, which is then linked to inositol.^[3] The oxidized, disulfide form of mycothiol (MSSM) is called mycothione, and is reduced to mycothiol by the flavoprotein mycothione reductase.^[4][5] Mycothiol biosynthesis and mycothiol-dependent enzymes such as mycothiol-dependent formaldehyde dehydrogenase and mycothione reductase have been proposed to be good drug targets for the development of treatments for tuberculosis.^[6][7]

Mycothiol

Names
IUPAC name (2R)-2-acetamido-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]-3-sulfanylpropanamide
Other names Mycothiol
Identifiers
CAS Number	192126-76-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16768 N
ChemSpider	10193006 N
KEGG	C06717 N
PubChem CID	441148
CompTox Dashboard (EPA)	DTXSID901027171
InChI InChI=1S/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1 N Key: MQBCDKMPXVYCGO-FQBKTPCVSA-N N InChI=1/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1 Key: MQBCDKMPXVYCGO-FQBKTPCVBG
SMILES CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@@H]2[C@@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)O)O)O)CO)O)O
Properties
Chemical formula	C17H30N2O12S
Molar mass	486.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

See also

• Glutathione, analogous function in other Bacteria
• Bacillithiol