16820-25-0

Basic information

• Product Name: (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID
• Synonyms: ALPHA-ALLYL-L-ALA;(S)-ALPHA-METHYL-ALLYLGLYCINE;-Allyl-L-Ala;A-ALLYL-L-ALA ;3-Butenoicacid,2-amino-2-methyl-,(2S)-(9CI);(2S)-2-Amino-2-methyl-3-butenoic acid;(2S)-(9CI)
• CAS NO: 16820-25-0
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 129.16
• Product Categories: GLYCINESCAFFOLD
• Mol File: 16820-25-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 245.3 °C at 760 mmHg
• Flash Point: 102.1 °C
• Appearance: /
• Density: 1.101 g/cm³
• Vapor Pressure: 0.00946mmHg at 25°C
• Refractive Index: 1.485
• CAS DataBase Reference: (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID(16820-25-0)
• EPA Substance Registry System: (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID(16820-25-0)

Safety Data

• Hazardous Substances Data: 16820-25-0(Hazardous Substances Data)

Usage

General Description

(S)-2-Amino-2-methyl-4-pentenoic acid is an organic compound that belongs to the class of alpha-amino acids. It is a chiral molecule that exists as a single enantiomer, and its structure consists of a pentenoic acid framework with a methyl group and an amino group attached to the second carbon atom. (S)-2-AMINO-2-METHYL-4-PENTENOIC ACID is a non-proteinogenic amino acid, meaning it is not incorporated into proteins during translation. It is primarily known for its potential as a synthetic intermediate in organic chemistry and pharmaceutical research. Its unique structural features and potential reactivity make it a valuable building block for the synthesis of complex organic molecules. Additionally, this compound may have potential biological activities and therapeutic applications that warrant further investigation.

InChI:InChI=1/C5H9NO2/c1-3-5(2,6)4(7)8/h3H,1,6H2,2H3,(H,7,8)/t5-/m0/s1

Upstream product

• 121704-28-7 N-Methoxyacetyl-α-methyl-α-vinylglycine 
• 16820-23-8 2,4-dimethyl-4-vinyl-4H-oxazol-5-one 
• 151074-94-1 (+)-(2S)-Methyl 4,4-dibromo-2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>-3-butenoate 
• 151074-90-7 (+)-(2S)-Methyl 2-methyl-2-<(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl>buten-3-oate 
• 314774-36-2 (4S,5R)-4-Methyl-2-phenyl-5-phenylselanylmethyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 314774-43-1 (E)-(S)-2-Benzoylamino-2-methyl-4-phenylselanyl-but-3-enoic acid methyl ester 
• 151074-95-2 (S)-4-Bromo-2-methyl-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-but-3-ynoic acid 

Downstream Products

• 1015251-57-6 (S)-2-(benzyloxycarbonylamino)-2-methylbut-3-enoic acid 

Relevant articles and documents

One-Pot Vinylation of Azlactones: Fast Access to Enantioenriched α-Vinyl Quaternary Amino Acids

We report a fast one-pot protocol for the direct vinylation of azlactones [oxazol-5-(4H)-ones] by using as a key step an aldol addition with 2-(phenylselenenyl)acetaldehyde followed by dehydroxyselenation. The acid hydrolysis of the oxazolone ring gave the desired fully deprotected α-vinyl quaternary α-amino acids in almost quantitative yields. An enantioselective variant of the method was also developed by using catalytic chiral bases. The use of Sharpless ligand (DHQD)2PHAL produced the final quaternary amino acids in good overall yields (62–78 %) and with ee values up to 86 %. Scaling up the optimized protocol to gram quantities did not affect the yields and ee values. We also demonstrated that the vinyl moiety installed onto the oxazolone ring can be exploited as a handle for the attachment of aryl groups through a Heck coupling reaction.

Organoselenium-based entry into versatile, α-(2-tributylstannyl)vinyl amino acids in scalemic form: A new route to vinyl stannanes [14]

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Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.