Bacillithiol: Difference between revisions

| verifiedrevid = 444244574

| Name = Bacillithiol

| Reference=

| ImageFile = Bacillithiol.svg

| ImageSize = 260px

| ImageName = 7-(beta-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

| IUPACName =

| OtherNames=

| CASNo_Ref = {{cascite|correct|??}}

| CASNo =

| PubChem = 42614123

| ChemSpiderID = 24604693

| SMILES = C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H](CC(=O)O)C(=O)O)NC(=O)[C@H](CS)N)O)O)O

| InChI = 1/C13H22N2O10S/c14-4(3-26)11(21)15-8-10(20)9(19)6(2-16)25-13(8)24-5(12(22)23)1-7(17)18/h4-6,8-10,13,16,19-20,26H,1-3,14H2,(H,15,21)(H,17,18)(H,22,23)/t4-,5-,6+,8+,9+,10+,13-/m0/s1

| InChIKey = UHNHELGKNQMNGF-AOQKXWSCBS

| StdInChI = 1S/C13H22N2O10S/c14-4(3-26)11(21)15-8-10(20)9(19)6(2-16)25-13(8)24-5(12(22)23)1-7(17)18/h4-6,8-10,13,16,19-20,26H,1-3,14H2,(H,15,21)(H,17,18)(H,22,23)/t4-,5-,6+,8+,9+,10+,13-/m0/s1

| StdInChIKey = UHNHELGKNQMNGF-AOQKXWSCSA-N

| Formula = C₁₃H_22N₂O₁₀S

| MolarMass = 398.39 g/mol

| ExactMass = 391.10 g/mol

| MeltingPt =

'''Bacillithiol''' (BSH or Cys-GlcN-mal) is a [[thiol]] compound found in ''[[Bacillus]]'' species.<ref name=Newton>{{Cite pmid|19578333}}</ref> Chemically, it is a glycoside formed between <small>L</small>-cysteinyl-<small>D</small>-glucosamine and [[malic acid]]. It was isolated and identified (as its bacillithiol-S-[[bimane]] derivative) in 2009 from ''[[Staphylococcus aureus]]'' and ''[[Deinococcus radiodurans]]'',<ref name=Newton/> although it was first detected in 2007, as an unidentified thiol in ''[[Bacillus anthracis]]''.<ref>{{Cite pmid|17323930}}</ref> The naturally occurring free thiol form of bacillithiol has since been synthesised and characterised along with its biosynthetic precursors and its symmetrical disulfide.<ref name="pmid21751306">{{cite journal |author=S. V. Sharma, V. K. Jothivasan, G. L. Newton, H. Upton, J. I.Wakabayashi, M. G. Kane, A. A. Roberts, M. Rawat, J. J. La Clair, and C. J. Hamilton. |title=Chemical and Chemoenzymatic Syntheses of Bacillithiol: A Unique Low-Molecular-Weight Thiol amongst Low G + C Gram-Positive Bacteria|journal=Angew. Chem. Int. Ed. |volume=50 |issue=31 |pages=7101–7104 |year=2011 |month=July |pmid=21751306 |doi=10.1002/anie.201100196}}</ref> Bacillithiol appears to participate in the sensing of [[peroxide]]s by ''Bacillus'',<ref>{{Cite pmid|17502599}}</ref> but may also substitute for [[glutathione]], which is the most common intracellular thiol in other organisms.<ref name=Newton/> Some of genes involved in the biosynthesis of bacillithiol were identified and characterized in 2010.<ref name="pmid20308541">{{cite journal |author=Gaballa A, Newton GL, Antelmann H, ''et al.'' |title=Biosynthesis and functions of bacillithiol, a major low-molecular-weight thiol in Bacilli |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=107 |issue=14 |pages=6482–6 |year=2010 |month=April |pmid=20308541 |doi=10.1073/pnas.1000928107 |url= |pmc=2851989}}</ref> Bacteria engineered to be deficient in bacillithiol demonstrated increased sensitivity to various electrophilic [[xenobiotic]] compounds, including the antibiotic [[fosfomycin]], suggesting that in these organisms the mechanism of [[Fosfomycin#Resistance|fosfomycin resistance]] relies on the presence of bacillithiol.<ref name="pmid20308541"/> Kinetic studies have also established that bacillithiol is a preferred thiol substrate for FosB compared to [[cysteine]].<ref name="pmid21751306" />

==See also==

*[[Mycothiol]]

==References==

[[Category:Glucosamines]]