23152-29-6

Usage

Uses

Used in Pharmaceutical Industry:
Virginiamycin S1 is used as a synergistic component in the Virginiamycin complex for its antimicrobial properties. It works in conjunction with ostreogrycin A to enhance the effectiveness of the antibiotic mixture.
Used in Agricultural Industry:
Virginiamycin S1 is used as an additive in the livestock and poultry industries to promote growth and improve feed efficiency. Its antimicrobial properties help prevent and control bacterial infections in animals, contributing to better health and productivity.
Used in Research and Development:
Virginiamycin S1 is utilized in scientific research to study the mechanisms of antibiotic action and resistance, as well as to develop new drugs and therapies based on its synergistic properties with other antibiotics.

Biological Activity

virginiamycin s1 is a macrolide antibiotic that reversibly inhibits protein synthesis [1][2][3].virginiamycin complex contains two antibiotics, virginiamycin m1 and virginiamycin s1. streptogramins are divided into class a and class b based on their structures. virginiamycin s1 is a member of the streptogramin b group of antibiotics, which bind the peptide exit tunnel to inhibit the elongation stage of translation. they show good bactericidal activity against methicillin-resistant s. aureus (mrsa), although resistance in mrsa is conferred by the cfr gene. virginiamycin m1 has activity against gram-positive and in select cases gram-negative bacteria. combination of group a and b streptogramins exhibit bactericidal activity [1]. virginiamycin s1 acted synergistically with virginiamycin m1 to irreversibly inhibit protein synthesis in bacteria. in cell-free systems, virginiamycin m1 and virginiamycin s1 bound to the large ribosomal subunit, and the affinity of ribosomes for vs is increased by vm [2][3].

InChI:InChI=1/C43H49N7O10/c1-4-29-40(56)49-21-12-17-30(49)41(57)48(3)32(23-26-13-7-5-8-14-26)42(58)50-22-19-28(51)24-31(50)37(53)47-35(27-15-9-6-10-16-27)43(59)60-25(2)34(38(54)45-29)46-39(55)36-33(52)18-11-20-44-36/h5-11,13-16,18,20,25,29-32,34-35,52H,4,12,17,19,21-24H2,1-3H3,(H,45,54)(H,46,55)(H,47,53)

Upstream product

• 102410-74-2 Fmoc-Thr(H-MePhe-4Kps-Phg-)-D-Abu-Pro-OH*HCl 
• 102410-73-1 Fmoc-Thr(Boc-MePhe-4Kps-Phg-)-D-Abu-Pro-OBu^t 
• 102410-80-0 Pic(3-OH)-Thr(Boc-MePhe-4Kps-Phg-)-D-Abu-Pro-OBu^t 
• 102410-75-3 ((3S,6S,15S,16R,19S,22S)-3-Benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 127092-11-9 3-(2,4-Dinitro-phenoxy)-pyridine-2-carboxylic acid (3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-amide 
• 127106-17-6 Carbonic acid 2-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester 2,2,2-trichloro-ethyl ester 
• 127106-16-5 Carbonic acid allyl ester 2-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester 
• 102410-81-1 Pic(3-OH)-Thr(H-MePhe-4Kps-Phg-)-D-Abu-Pro-OH*2HCl 
• 874-24-8 3-hydroxypyridine-2-carboxylic acid 
• 102410-76-4 (3S,6S,15S,16R,19S,22S)-15-Amino-3-benzyl-12-ethyl-4,16-dimethyl-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacosane-2,5,11,14,18,21,24-heptaone 
• 137407-83-1 Carbonic acid 2-((3S,6S,12R,15S,16R,19S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester tert-butyl ester 
• 117505-35-8 2-({1-[2-(2-[(3-Hydroxy-pyridine-2-carbonyl)-amino]-3-{2-[(4-oxo-piperidine-2-carbonyl)-amino]-2-phenyl-acetoxy}-butyrylamino)-butyryl]-pyrrolidine-2-carbonyl}-methyl-amino)-3-phenyl-propionic acid; compound with trifluoro-acetic acid 

Downstream Products

• 127092-11-9 3-(2,4-Dinitro-phenoxy)-pyridine-2-carboxylic acid (3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-amide 
• 137407-72-8 C₅₁H₅₇N₇O₁₃ 
• 137407-73-9 C₅₁H₅₈N₈O₁₂ 
• 137407-77-3 C₅₂H₆₅N₇O₁₅ 
• 137407-82-0 (S)-2-({(S)-1-[(R)-2-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-butyryl]-pyrrolidine-2-carbonyl}-methyl-amino)-3-phenyl-propionic acid benzyl ester; compound with trifluoro-acetic acid 
• 137407-74-0 2-[((S)-{(1R,2S)-2-[(3-Hydroxy-pyridine-2-carbonyl)-amino]-1-methyl-2-[(R)-1-((S)-2-methylcarbamoyl-pyrrolidine-1-carbonyl)-propylcarbamoyl]-ethoxycarbonyl}-phenyl-methyl)-carbamoyl]-4-oxo-piperidine-1-carboxylic acid benzyl ester 
• 137407-79-5 (S)-2-{[(S)-1-((R)-2-{(2S,3R)-2-[tert-Butoxycarbonyl-(3-tert-butoxycarbonyloxy-pyridine-2-carbonyl)-amino]-3-hydroxy-butyrylamino}-butyryl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionic acid benzyl ester 
• 127106-18-7 (S)-{[1-((S)-2-{[(S)-1-((R)-2-{(2S,3R)-3-Hydroxy-2-[(3-hydroxy-pyridine-2-carbonyl)-amino]-butyrylamino}-butyryl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyl)-4-oxo-piperidine-2-carbonyl]-amino}-phenyl-acetic acid 
• 137407-78-4 (S)-2-{[(S)-1-((R)-2-{(2S,3R)-3-Hydroxy-2-[(3-hydroxy-pyridine-2-carbonyl)-amino]-butyrylamino}-butyryl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionic acid benzyl ester 
• 131286-33-4 (S)-2-{[(S)-1-((R)-2-{(2S,3R)-3-Hydroxy-2-[(3-hydroxy-pyridine-2-carbonyl)-amino]-butyrylamino}-butyryl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionic acid 
• 3828-66-8 (S)-[(4-Oxo-piperidine-2-carbonyl)-amino]-phenyl-acetic acid 
• 117505-35-8 (S)-2-({(S)-1-[(R)-2-((2S,3R)-2-[(3-Hydroxy-pyridine-2-carbonyl)-amino]-3-{(S)-2-[(4-oxo-piperidine-2-carbonyl)-amino]-2-phenyl-acetoxy}-butyrylamino)-butyryl]-pyrrolidine-2-carbonyl}-methyl-amino)-3-phenyl-propionic acid; compound with trifluoro-acetic acid 
• 137407-83-1 Carbonic acid 2-((3S,6S,12R,15S,16R,19S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester tert-butyl ester 
• 129446-52-2 virginiamycin S aminoethyloxime hydrochloride 

Relevant academic research and scientific papers

UNIQUE 1'-O-BOC PROTECTION OF VIRGINIAMYCIN S AND RESULTING RESISTANCE AGAINST SODIUM HYDROXIDE

The picolinic hydroxyl in Virginiamycin S1 (VS%1; 1a) can be protected with di-tert-butyloxycarbonate affording the tert-butyloxycarbonyl derivative thus yielding VS1-1'-O-Boc (1b) in a fast and quantitative conversion without concomitant betaine (1c) formation.Once protected however, the lactone bond in 1b can no longer be cleaved under mild alkaline conditions.A possible explanation is given.

THE DEPENDENCE OF ENDOPEPTOLYSIS ON THE SEQUENTIAL CHIRALITY EXEMPLIFIED BY A SIMPLIFIED PREPARATION OF THE 4>-EPIMER OF VIRGINIAMYCIN S.

The 4-epimer of Virginiamycin S (VS-epi4) containing the heterochiral triad L-Pro3-D-MePhe4-L-(γOxo)Pec5 is found to be resistant against acidic hydrolysis in contrast to the native VS possessing the L3,L4,L5-sequence.This allows a simplified protocol for its isolation, and exemplifies previous findings (ref. 1) about the easy endopeptolysis of homochiral triads.

A SEARCH FOR PHENOLIC PROTECTION IN VIRGINIAMYCIN S

In order to be able to mask the hydroxyl grouping of the pipecolic acid residue in Virginiamycin during alkaline (NaOH) and acidic (Tfa) break-down procedures and to use peptidic fragments coming thereof for further reconstitution by classical peptide synthesis procedures, we have investigated several candidates for protection/deprotection.Thus the phenacyl derivatives (4 and 5), the allyloxycarbonyl derivative (6), the trichloroethyloxycarbonyl derivatives (8 and 9) and the 2,4-dinitrophenyl derivative (10) have been prepared.Among these none were stable in aqueous basic conditions.The Alloc- (6) the Troc- (8) and Dnp-derivative (10) may have some applications under acidic conditions.

CYCLIZATION OF A LINEAR PRECURSOR OF VIRGINIAMYCIN S1 (VS1) MEDIATED BY WOODWARD'S REAGENT K.

Cyclization of a model linear hexapeptide (VS1 linear peptide, 1) was achieved by using N-ethyl-5-phenylisoxazolinium-3'-sulfonate (Woodward's reagent K).Yields of the resulting cyclic product 2 were quite low (ca. 15percent) in various solvents.The yield in CH2Cl2 increased substantially when the reaction was carried out under free air instead of N2 atmosphere.