Pristinamycin IIA: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid =

| IUPAC_name = 8,9,14,15,24,25--14-hydroxy-4,12-dimethyl-3-(1-methylethyl)(,,,,,)--21,18-nitrolo-,-pyrrolo\[2,1-c][1,8,4,19]-dioxadiazacyclotetracosine-1,7,16,22(,)-tetrone

| image = Streptogramin A.svg

<!--Clinical data-->

| tradename =

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8W4UOL59AZ

| CAS_number = 21411-53-0

| PubChem = 5354042

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 9997

| ChemSpiderID = 10222381

<!--Chemical data-->

| chemical_formula =

| C=28|H=35|N=3|O=7

| smiles = C[C@@H]1/C=C/C(=O)NC/C=C/C(=C/[C@H](CC(=O)Cc2nc(co2)C(=O)N3CCC=C3C(=O)O[C@@H]1C(C)C)O)/C

| StdInChI = 1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5+,10-9+,18-13+/t19-,20-,26-/m1/s1

| StdInChIKey = DAIKHDNSXMZDCU-FQTGFAPKSA-N

| synonyms = Mikamycin A; Virginiamycin M1

'''Pristinamycin IIA''' is a [[macrolide antibiotic]]. It is a member of the [[streptogramin A]] group of antibiotics and one component of [[pristinamycin]] (the other being [[pristinamycin IA]]).<ref>{{cite journal | vauthors = Laforest H, Fourgeaud M, Richet H, Lagrange PH | title = Comparative in vitro activities of pristinamycin, its components, and other antimicrobial agents against anaerobic bacteria | journal = Antimicrobial Agents and Chemotherapy | volume = 32 | issue = 7 | pages = 1094–1096 | date = July 1988 | pmid = 3142342 | pmc = 172352 | doi = 10.1128/AAC.32.7.1094 }}</ref> Pristinamycin IIA was first isolated from the [[Streptomyces virginiae]], but has been isolated from other microorganisms and thus has been given a variety of other names such as Virginiamycin M1, Mikamycin A, and Streptogramin A.<ref name="Kingston_1980"> {{cite journal | vauthors = Kingston DG, Kolpak MX |date= August 1980|title= Biosynthesis of antibiotics of the virginiamycin family. 1. Biosynthesis of virginiamycin M1: determination of the labeling pattern by the use of stable isotope techniques |url= https://pubs.acs.org/doi/pdf/10.1021/ja00538a070|journal= Journal of the American Chemical Society|volume= 102|issue= 18|pages= 5964–5966|doi= 10.1021/ja00538a070|access-date=29 May 2022}} </ref> Pristinamycin IIA structure was determined by chemical and instrumental techniques, including X-ray crystallography.<ref name="Kingston_1980" /><ref> {{cite journal | vauthors = Delpierre GR, Eastwood FW, Gream GE, Kingston DG, Sarin PS, Todd L, Williams DH | title = Antibiotics of the ostreogrycin complex. II. Structure of ostreogrycin A | journal = Journal of the Chemical Society, Perkin Transactions 1 | volume = 19 | pages = 1653–1669 | date = 1966 | pmid = 5950461 | doi = 10.1039/j39660001653 }} </ref> Pristinamycin IIA is of interest from a biosynthetic viewpoint because it contains the unusual dehydroproline and [[oxazole]] ring systems.<ref name="Kingston_1980" /> The only experimental evidence bearing on the formation of the [[oxazole]] ring is found in work on the biosynthesis of the alkaloid annuloline.<ref name="Kingston_1980" /><ref> {{cite journal | vauthors = O'Donovan DG, Horan HJ |date= 1971|title= The biosynthesis of annuloline, a unique oxazole alkaloid |journal= Journal of the Chemical Society C: Organic|volume= 1|pages= 331–334|doi= 10.1039/J39710000331 }} </ref>

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==Biosynthesis==

Pristinamycin IIA biosynthesis is presumed to proceed through the acetate pathway and was determined through the feeding of ³H and ¹³C precursors to [[Streptomyces virginiae]] strain PDT-30.<ref name="Kingston_1980" /> When fed [2-¹³C]-acetate the 13C [[NMR]] Spectra showed signals corresponding to carbons 5, 9, 10a, 11, 13, and 15 seen in the biosynthesis scheme.<ref name="Kingston_1980" /> In addition, [[methionine]] was found to donate its methyl group specifically to carbon-3 (seen in the biosynthesis scheme) by studies with L-[methyl-¹³C] methionine.<ref name="Kingston_1980" /> With this data and the known incorporation of [[proline]], [[methionine]], [[serine]], and [[glycine]] into the antibiotic along with the assumption that carbon atoms 1, la, lb, and 2 are derived from [[valine]] or [[isobutyric acid]], allows for a tentative pathway for the biosynthesis of Pristinamycin IIA to be deduced.<ref name="Kingston_1980" />

[[File:Virginiamycin M1 Biosynthesis 3.tif|thumb|left|420x420px|Biosynthesis of Pristinamycin IIA<ref name="Kingston_1980" />]]

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== See also ==

* [[Pristinamycin IIB]]

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== References ==

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[[Category:Oxazoles]]

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