189249-10-3

Basic information

• Product Name: Fomc-cis-L-hydroxyproline-OH
• Synonyms: Fomc-cis-L-hydroxyproline-OH;(2S,4S)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;(2S,4S)-1-(((9H-Fluoren-9y l)methoxy)carbony l)-4hydroxypyrrolidine-2-carboxy lic aci;(4S)-1-Fmoc-4-hydroxy-L-proline;(9H-Fluoren-9-yl)MethOxy]Carbonyl Cis-Hyp-OH
• CAS NO: 189249-10-3
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.38
• Mol File: 189249-10-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Fomc-cis-L-hydroxyproline-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fomc-cis-L-hydroxyproline-OH(189249-10-3)
• EPA Substance Registry System: Fomc-cis-L-hydroxyproline-OH(189249-10-3)

Safety Data

• Hazardous Substances Data: 189249-10-3(Hazardous Substances Data)

Usage

General Description

Fomc-cis-L-hydroxyproline-OH is a chemical compound consisting of a cis isomer of L-hydroxyproline with a formula of C12H13NO4. It is commonly used in the field of organic synthesis, biochemical research, and pharmaceutical development. Fomc-cis-L-hydroxyproline-OH is often used as a building block in peptide synthesis, particularly for the creation of peptides with specific structural and functional properties. It can also be utilized as a chiral auxiliary in asymmetric synthesis and as a component in the development of new drugs and therapies. Overall, Fomc-cis-L-hydroxyproline-OH plays a significant role in various scientific and medical applications due to its unique chemical properties and structural characteristics.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 618-27-9 hydroxy L-proline 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 147-85-3 L-proline 

Downstream Products

• 847978-87-4 [1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 1190083-09-0 C₄₆H₇₁N₁₁O₁₂S₂ 
• 268729-12-0 N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline 

Relevant articles and documents

Evidence for a stereoelectronic effect in human oxygen sensing

How PHDs achieve specificity: trans-4-prolyl hydroxylation of the transcription factor HIF occurs with stereochemical retention. Substrate-analogue studies show how the von Hippel Lindau tumor suppressor protein (pVHL) and the oxygen-sensing hydroxylases (PHDs) achieve specificity for hydroxy prolyl/prolyl residues for the C4-exo/endo prolyl conformations, respectively.

Total Synthesis of the Death Cap Toxin Phalloidin: Atropoisomer Selectivity Explained by Molecular-Dynamics Simulations

Phallotoxins and amatoxins are a group of prominent peptide toxins produced by the death cap mushroom Amanita phalloides. Phalloidin is a bicyclic cyclopeptide with an unusual tryptathionin thioether bridge. It is a potent stabilizer of filamentous actin and in a fluorescently labeled form widely used as a probe for actin binding. Herein, we report the enantioselective synthesis of the key amino acid (2S,4R)-4,5-dihydroxy-leucine as a basis for the first total synthesis of phalloidin, which was accomplished by two different synthesis strategies. Molecular-dynamics simulations provided insights into the conformational flexibility of peptide intermediates of different reaction strategies and showed that this flexibility is critical for the formation of atropoisomers. By simulating the intermediates, rather than the final product, molecular-dynamics simulations will become a decisive tool in orchestrating the sequence of ring formation reactions of complex cyclic peptides.

The impact of pyrrolidine hydroxylation on the conformation of proline-containing peptides

(Chemical Equation Presented) A series of eight dipeptides of the general formula Ac-Phe-Pro*-NHMe was synthesized and the thermodynamics of the cis → trans isomerization about the central amide bond were studied by NMR. Pro* represents the following prol