144701-24-6

Basic information

• Product Name: FMOC-D-NVA-OH
• Synonyms: Fmoc-D-NVal-OH;Fmoc-D-norvaline99%;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-NORVALINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-2-AMINOPENTANOIC ACID;N-ALPHA-FMOC-D-NORVALINE;RARECHEM EM WB 0171;FMOC-D-APE(2)-OH;FMOC-D-2-AMINOVALERIC ACID
• CAS NO: 144701-24-6
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.39
• Mol File: 144701-24-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 152-154°C
• Boiling Point: 557.9 °C at 760 mmHg
• Flash Point: 291.2 °C
• Appearance: White powder
• Density: 1.23 g/cm³
• Storage Temp.: 2-8°C
• PKA: 3.91±0.20(Predicted)
• CAS DataBase Reference: FMOC-D-NVA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-NVA-OH(144701-24-6)
• EPA Substance Registry System: FMOC-D-NVA-OH(144701-24-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 144701-24-6(Hazardous Substances Data)

Usage

Description

FMOC-D-NVA-OH, also known as 9-fluorenylmethoxycarbonyl-D-norvaline, is a synthetic amino acid derivative used in various applications due to its unique chemical properties. It is a white powder and serves as a crucial intermediate in organic synthesis.

Uses

Used in Organic Synthesis:
FMOC-D-NVA-OH is used as an intermediate for organic synthesis, particularly in the development of pharmaceuticals and other bioactive compounds. Its unique structure allows for the creation of complex molecules with specific properties, making it a valuable tool in the field of chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, FMOC-D-NVA-OH is used as a building block for the synthesis of various drugs and drug candidates. Its incorporation into the molecular structure can enhance the pharmacological properties of the final product, leading to improved efficacy and safety profiles.
Used in Peptide Synthesis:
FMOC-D-NVA-OH is also utilized in the synthesis of peptides, which are short chains of amino acids that serve as the building blocks of proteins. The D-configuration of the norvaline in FMOC-D-NVA-OH allows for the creation of non-natural peptides with unique properties, which can be used for various therapeutic applications.
Used in Research and Development:
In the field of research and development, FMOC-D-NVA-OH is employed as a reagent for the study of protein structure and function. Its ability to form stable peptide bonds and its compatibility with various chemical reactions make it an essential tool for understanding the complex interactions between proteins and other biomolecules.

Upstream product

• 760-78-1 2-aminopentanoic acid 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 1821-02-9 2-oxopentanoic acid 
• 2013-12-9 D-norvaline 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 749250-57-5 C₃₀H₃₁N₃O₅ 
• 439082-60-7 (R)-2-propylpiperazine 

Relevant articles and documents

Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases

Liquid chromatographic enantiomer separation and simultaneous determination of chemical and enantiomeric purity of α-amino acids and their methyl esters as N-fluorenylmethoxycarbonyl (FMOC) derivatives was performed on three covalently bonded type chiral stationary phases (CSPs) derived from amylose derivatives. The enantiomer separation of α-amino acid esters as N-FMOC derivatives was better than that of the corresponding acids, especially for CSP 1 and 2. Chemical impurities as the corresponding racemic acids present in several commercially available racemic amino acid methyl esters were observed to be 0.49–17.50%. Enantiomeric impurities of several commercially available L-amino acid methyl esters were found to be 0.03–0.58%, whereas chemical impurities as the corresponding racemic acids present in the same analytes were found to be 0.13–13.62%. This developed analytical method will be useful for the determination of chemical and enantiomeric purity of α-amino acids and/or esters as N-FMOC derivatives using amylose-derived CSPs.

Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles

(Chemical Equation Presented) Homochiral α-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde. The key feature of the sequence is a highly selective tandem Mitsunobu/3,3-sigmatropic rearrangement of hydrazoic acid that procures enantiomerically enriched allylic azides. The sequence is either terminated by oxidative cleavage to provide amino acids or by ring-closing metathesis to provide heterocycles or carbocycles bearing nitrogen.