133413-70-4

Basic information

• Product Name: PF 1022A
• Synonyms: PF 1022A;Cyclo(D-2-hydroxypropanoyl-N-methyl-L-leucyl-3-phenyl-D-2-hydroxypropanoyl-N-methyl-L-leucyl-D-2-hydroxypropanoyl-N-methyl-L-leucyl-3-phenyl-D-2-hydroxypropanoyl-N-methyl-L-leucyl)
• CAS NO: 133413-70-4
• Molecular Formula: C52H76N4O12
• Molecular Weight: 949.17944
• EINECS: 444-350-6
• Mol File: 133413-70-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 89-92 °C
• Boiling Point: 1086.6°Cat760mmHg
• Flash Point: 610.9°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.489
• PKA: -1.09±0.70(Predicted)
• CAS DataBase Reference: PF 1022A(CAS DataBase Reference)
• NIST Chemistry Reference: PF 1022A(133413-70-4)
• EPA Substance Registry System: PF 1022A(133413-70-4)

Safety Data

• Hazardous Substances Data: 133413-70-4(Hazardous Substances Data)

Usage

General Description

PF 1022A is a natural, semi-synthetic antibiotic compound derived from the fermentation of a bacteria called Mycobacterium tubicidypticum. It belongs to the class of compounds called macrolides, which are characterized by a macrocyclic lactone ring in their structure. PF 1022A has been documented to have potent antifungal and anthelmintic properties, making it highly effective against a variety of fungal infections and parasitic worms. It works by inhibiting protein synthesis in the targeted organisms, disrupting their cellular function and ultimately leading to their death. Due to its wide spectrum of activity and low toxicity profile, PF 1022A has found applications in the agricultural and veterinary industries as a valuable tool in the management of parasitic and fungal diseases.

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

• 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 
• 153052-70-1 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate 
• 53363-89-6 N-t-butoxycarbonyl-N-methyl-L-leucine 
• 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 articles and documents

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.

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.

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.