114301-25-6

Basic information

• Product Name: Rhizocticin A
• Synonyms: Rhizocticin A
• CAS NO: 114301-25-6
• Molecular Formula: C11H22N5O6P
• Molecular Weight: 351.3
• Mol File: 114301-25-6.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.64g/cm³
• Refractive Index: 1.64
• PKA: 2.15±0.10(Predicted)
• CAS DataBase Reference: Rhizocticin A(CAS DataBase Reference)
• NIST Chemistry Reference: Rhizocticin A(114301-25-6)
• EPA Substance Registry System: Rhizocticin A(114301-25-6)

Safety Data

• Hazardous Substances Data: 114301-25-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H22N5O6P/c12-7(3-1-5-15-11(13)14)9(17)16-8(10(18)19)4-2-6-23(20,21)22/h2,4,7-8H,1,3,5-6,12H2,(H,16,17)(H,18,19)(H4,13,14,15)(H2,20,21,22)/b4-2+

Upstream product

• 126587-36-8 (4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate 
• 130532-55-7 (4S)-3-N-(tert-butoxycarbonyl)-4-<3-hydroxy-(1Z)-propenyl>-2,2-dimethyl-1,3-oxazolidine 
• 1449748-45-1 (S,Z)-methyl 2-(tert-butoxycarbonylamino)-5-(dimethoxyphosphoryl)pent-3-enoate 
• 1449748-42-8 (S,Z)-tert-butyl 4-(3-bromoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1449748-43-9 (S,Z)-tert-butyl 4-(3-(dimethoxyphosphoryl)prop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1449748-44-0 (S,Z)-tert-butyl 5-(dimethoxyphosphoryl)-1-hydroxypent-3-en-2-ylcarbamate 
• 1449748-52-0 C₃₂H₅₂N₅O₁₁PS 
• 1449748-51-9 C₃₁H₅₂N₅O₁₀PS 
• 1449748-50-8 C₈H₁₆NO₅P*C₂HF₃O₂ 
• 1449748-48-4 C₇H₁₆NO₄P*C₂HF₃O₂ 
• 114301-26-7 L-valyl-L-arginyl-5-phosphono-L-cis-3,4-didehydronorvaline 

Downstream Products

• 114376-26-0 L-2-amino-5-phosphono-3-cis-pentenoic acid 

Related news

Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A (cas 114301-25-6) and Plumbemycin A09/04/2019

Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report t...detailed

Relevant articles and documents

Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A

Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5- phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi.

Rhizocticins - New Phosphono-Oligopeptides with Antifungal Activity

The widely used and well-known bacterial strain Bacillus subtilis ATCC 6633 was found to produce two novel, antifungal hydrophilic peptide antibiotics, L-arginyl-L-2-amino-5-phosphono-3-cis-pentenoic acid (L-Arg-L-APPA, rhizocticin A) and L-valyl-L-arginyl-L-2-amino-5-phosphono-3-cis-pentenoic acid (L-Val-L-Arg-L-APPA, rhizocticin B).Besides rhizocticin A and B, the main components, small amounts of related tripeptides were detected.Instead of the L-Val of rhizocticin B they contain L-Ile or L-Leu and are referred to as rhizocticin C and D, respectively.The C-terminal residue was identified by NMR spectroscopy as the unsaturated phosphono amino acid L-APPA, known till now only as D enantiomer.Enzymatic cleavages of rhizocticin B yielded both L-APPA and rhizocticin A.