96-81-1

Basic information

• Product Name: N-Acetyl-L-valine
• Synonyms: Ac-L-Val-OH;N-alpha-Actetyl-L-valine;(S)-2-ACETAMIDO-3-METHYLBUTANOIC ACID;N-ACETYL-L-VALINE extrapure for biochemistry;(2S)-2-acetamido-3-methylbutanoic acid;(2S)-2-acetamido-3-methyl-butanoic acid;(2S)-2-acetamido-3-methyl-butyric acid;L-Valine, N-acetyl-Valine, N-acetyl-, L-Ac-L-Val-OH
• CAS NO: 96-81-1
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.18
• EINECS: 202-537-8
• Product Categories: Amino Acid Derivatives;Amino Acids;amino acid;amino
• Mol File: 96-81-1.mol
• Article Data: 41

Chemical Properties

• Melting Point: 163-167℃
• Boiling Point: 362.2 °C at 760 mmHg
• Flash Point: 172.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.094 g/cm³
• Storage Temp.: −20°C
• Solubility: soluble in Methanol
• PKA: 3.62±0.10(Predicted)
• CAS DataBase Reference: N-Acetyl-L-valine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-L-valine(96-81-1)
• EPA Substance Registry System: N-Acetyl-L-valine(96-81-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 96-81-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

Ac-Val-OH may be employed as a ligand for the meta-selective tert-alkylation reaction.

Definition

ChEBI: An L-valine derivative in which one of the amino hydrogens of L-valine has been replaced by an acetyl group.

General Description

Ac-Val-OH is an N-protected valine amino acid ligand. It participates in the 2,6-diolefination reaction of phenylacetic acids.

InChI:InChI=1/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1

Upstream product

• 64724-68-1 diethyl 2-N-acetylamino-2-isopropylmalonate 
• 6642-21-3 2-acetylamino-3-methyl-crotonic acid 
• 516-06-3 D,L-valine 
• 75-36-5 acetyl chloride 
• 72-18-4 L-valine 
• 64-19-7 acetic acid 
• 56430-36-5 (RS)-N-acetyl valine ethyl ester 
• 52152-47-3 N-acetyl-DL-valine methyl ester 
• 194661-11-5 N-Acetyl-D,L-valin-n-butylester 
• 21760-98-5 L-valine benzyl ester 
• 13893-45-3 valine ethyl ester 
• 4070-48-8 L-valine methyl ester 
• 96-81-1 N-acetyl-D,L-valine 
• 17623-72-2 2-methyl-4-iso-propyl-4H-oxazolin-5-one 

Downstream Products

• 17623-72-2 2-methyl-4-iso-propyl-4H-oxazolin-5-one 
• 52152-47-3 N-acetyl-DL-valine methyl ester 
• 91077-78-0 3-Acetyl-4-isopropyl-5-oxazolidinone 
• 473932-28-4 (S)-2-[2'-(2''-acetylamino-3''-methylbutyrylamino)phenylethynyl]benzoic acid methyl ester 
• 125679-71-2 (S)-3-Acetyl-4-isopropyl-oxazolidin-5-one 
• 923954-52-3 N-acetyl-ambo-valyl-ambo-alanine methyl ester 

Relevant articles and documents

Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres

Hepsin is a type II transmembrane serine protease (TTSP) associated with cell proliferation and overexpressed in several types of cancer including prostate cancer (PCa). Because of its significant role in cancer progression and metastasis, hepsin is an attractive protein as a potential therapeutic and diagnostic biomarker for PCa. Based on the reported Leu-Arg dipeptide-based hepsin inhibitors, we performed structural modification and determined in vitro hepsin- and matriptase-inhibitory activities. Comprehensive structure-activity relationship studies identified that the p-guanidinophenylalanine-based dipeptide analog 22a exhibited a strong hepsin-inhibitory activity (Ki = 50.5 nM) and 22-fold hepsin selectivity over matriptase. Compound 22a could be a prototype molecule for structural optimization of dipeptide-based hepsin inhibitors.

Bio- And Medicinally Compatible α-Amino-Acid Modification via Merging Photoredox and N-Heterocyclic Carbene Catalysis

An N-heterocyclic carbene and photoredox cocatalyzed α-amino-acid decarboxylative carbonylation reaction is presented. This method displays good scope generality, providing a direct pathway to access various downstream α-amino ketones under bio- and medicinally compatible conditions. Moreover, this strategy is appealing to chemical biology because it has great potential for the chemical modification of peptides or the late-stage synthesis of keto-peptides.

Oxidative functionalization of aliphatic and aromatic amino acid derivatives with H2O2 catalyzed by a nonheme imine based iron complex

The oxidation of a series of N-acetyl amino acid methyl esters with H2O2 catalyzed by a very simple iminopyridine iron(ii) complex 1 easily obtainable in situ by self-assembly of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 was investigated. Oxidation of protected aliphatic amino acids occurs at the α-C-H bond exclusively (N-AcAlaOMe) or in competition with the side-chain functionalization (N-AcValOMe and N-AcLeuOMe). N-AcProOMe is smoothly and cleanly oxidized with high regioselectivity affording exclusively C-5 oxidation products. Remarkably, complex 1 is also able to catalyze the oxidation of the aromatic N-AcPheOMe. A marked preference for the aromatic ring hydroxylation over Cα-H and benzylic C-H oxidation was observed, leading to the clean formation of tyrosine and its phenolic isomers.