133413-70-4

Usage

Uses

Used in Agricultural Industry:
PF 1022A is used as a fungicide for protecting crops from fungal infections. Its potent antifungal properties help in controlling a variety of fungal diseases, ensuring healthy growth and increased yield.
Used in Veterinary Medicine:
PF 1022A is used as an anthelmintic for treating parasitic worm infections in animals. Its effectiveness against a range of parasitic worms helps in maintaining the health of livestock and reducing the impact of parasitic diseases on animal welfare and productivity.
Used in Pharmaceutical Industry:
PF 1022A is used as a research compound for developing new drugs with antifungal and anthelmintic properties. Its unique mechanism of action and low toxicity profile make it a promising candidate for the development of novel therapeutics in the fight against fungal and parasitic infections.

InChI:InChI=1/C52H76N4O12/c1-31(2)25-39-49(61)65-35(9)45(57)53(11)42(28-34(7)8)52(64)68-44(30-38-23-19-16-20-24-38)48(60)56(14)40(26-32(3)4)50(62)66-36(10)46(58)54(12)41(27-33(5)6)51(63)67-43(47(59)55(39)13)29-37-21-17-15-18-22-37/h15-24,31-36,39-44H,25-30H2,1-14H3/t35-,36-,39+,40+,41+,42+,43-,44-/m1/s1

Upstream product

• 53363-89-6 N-t-butoxycarbonyl-N-methyl-L-leucine 
• 153052-70-1 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate 
• 153052-74-5 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactate 
• 160518-08-1 benzyl N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactate 
• 153153-72-1 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactate 
• 153052-72-3 N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactic acid 
• 153052-68-7 (2R)-1-(benzyloxy)-1-oxopropan-2-yl (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoate 
• 153052-71-2 Boc-L-MeLeu-D-PhLac-OH 
• 153052-69-8 (2R)-1-(benzyloxy)-1-oxopropan-2-yl (2S)-4-methyl-2-(methylamino)pentanoate 
• 153052-77-8 N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactyl-N-methyl-L-leucyl-3-phenyl-D-lactyl-N-methyl-L-leucyl-D-lactic acid 
• 170745-21-8 H-L-MeLeu-D-Lac-L-MeLeu-D-PhLac-L-MeLeu-D-Lac-L-MeLeu-D-PhLac-OH 

Downstream Products

• 189159-87-3 (3S,6R,9S,12R,15S,18R,21S,24R)-6-((1H-benzo[d]imidazol-2-yl)methyl)-18-benzyl-3,9,15,21-tetraisobutyl-4,10,12,16,22,24-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraazacyclotetracosan-2,5,8,11,14,17,20,23-octanone 
• 1379598-39-6 C₅₇H₈₄N₆O₁₄ 
• 1379598-40-9 C₅₃H₇₈N₆O₁₃ 
• 1379598-41-0 C₅₇H₈₄N₆O₁₃ 
• 1379598-42-1 C₅₅H₈₂N₈O₁₃ 
• 1379598-43-2 C₅₉H₈₈N₆O₁₃ 
• 1379598-44-3 C₅₃H₈₄N₆O₁₄ 

Relevant academic research and scientific papers

METHOD FOR THE SYNTHESIS OF CYCLIC DEPSIPEPTIDES

The present invention relates to a method for the synthesis of cyclic depsipeptides, in particular emodepside, from the open form.

Segment solid-phase total synthesis of the anthelmintic cyclooctadepsipeptides PF1022A and emodepside

Cyclodepsipeptides of the enniation, PF1022 and verticilide families represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now, no practicable solid-phase syntheses of these compounds have been accomplished, probably due to the problematic combination of N-methyl amino acids and hydroxycarboxylic acids. We report herein an efficient synthesis of the anthelmintic PF1022A and its commercial analogue emodepside on Kaiser and Wang resins. Our protocol provides the basis for the solid-phase synthesis of cyclodepsipeptide libraries with a high probability of anthelmintic, antibacterial or insecticidal activity.

Anthelmintic PF1022A: Stepwise solid-phase synthesis of a cyclodepsipeptide containing N-methyl amino acids

Cyclodepsipeptides of the enniation-, PF1022-, and verticilide-family represent a diverse class of highly interesting natural products with respect to their manifold biological activities. However, until now no stepwise solid-phase synthesis has been accomplished due to the difficult combination of N-methyl amino acids and hydroxycarboxylic acids. We report here the first stepwise solid-phase synthesis of the anthelmintic cyclooctadepsipeptide PF1022A based on an Fmoc/THP-ether protecting group strategy on Wang-resin. The standard conditions of our synthesis allow an unproblematic adaption to an automated peptide synthesizer.

PF1022A - A novel anthelmintic cyclooctadepsipeptide. Modification and exchange of the N-methyl leucine residues

The first structure-activity relationships of the anthelmintic cyclooctadepsipeptide PF1022A have been established via a systematic exchange of the leucine residues by a series of related N-alkylated amino acids. The data presented strongly suggest that (

A Highly Efficient Synthesis of the Anthelmintic Cyclooctadepsipeptide PF1022A

The potent anthelmintic cyclooctadepsipeptide PF1022A was synthesized by a series of fragment condensations starting from the known (S)-2-chloropropanoic acid and (S)-2-chloro-3-phenylpropanoic acid in eleven steps with a total yield of 13percent.Noteworthy is the excellent yield of the BOP-Cl mediated lactamization reaction of the linear precursor 17 leading to the 24-membered macrocycle.

Total Synthesis of the Anthelmintic Cyclodepsipeptide, PF1022A

The anthelmintic cyclooctadepsipeptide PF1022A and its antipode were synthesized starting from L-Nα-Boc-leucine (for PF1022A), D-N4a-Boc-leucine (for the antipode), L-lactic acid, and L-phenyllactic acid using Mitsunobu reaction and/