210345-89-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-AMINOMETHYL-4-METHYL-PENTANOIC ACID is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs with improved biological activity and pharmacokinetic properties.
Used in Medicinal Chemistry:
(R)-2-AMINOMETHYL-4-METHYL-PENTANOIC ACID is used as a chiral amino acid in medicinal chemistry for the design and synthesis of drug molecules, enhancing their efficacy and selectivity.
Used in Food Science:
(R)-2-AMINOMETHYL-4-METHYL-PENTANOIC ACID is used in food science for the development of new food additives or ingredients, potentially improving the taste, texture, or nutritional value of food products.
Used in Agriculture:
(R)-2-AMINOMETHYL-4-METHYL-PENTANOIC ACID is used in agriculture for the development of new agrochemicals or as a component in fertilizers, enhancing crop yield and quality.
Used in Materials Science:
(R)-2-AMINOMETHYL-4-METHYL-PENTANOIC ACID is used in materials science for the development of new bioconjugates and biomaterials, potentially improving the properties of these materials for various applications.
Used in Research and Development:
(R)-2-AMINOMETHYL-4-METHYL-PENTANOIC ACID is used in research and development for the exploration of new chemical entities, expanding the scope of chemical and biological knowledge and fostering innovation in various industries.

Upstream product

• 210345-88-3 (R)-2-(Benzoylamino-methyl)-4-methyl-pentanoic acid 
• 501330-99-0 (4R)-isobutyl-2-((S)-1-phenylethyl)-isoxazolidin-5-one 
• 61-90-5 L-leucine 
• 28659-87-2 (S)-2-bromo-4-methylpentanoic acid 
• 132606-01-0 (2R)-([{(benzyloxy)carbonyl}amino]methyl)-4-methylpentanoic acid 
• 631899-15-5 (2S)-([{(benzyloxy)carbonyl}amino]methyl)-4-methylpentanoic acid 
• 1415986-78-5 S-ethyl (2R)-2-(dibenzylamino)methyl-4-methylpentanethioate 
• 1415986-81-0 (2R)-2-(dibenzylamino)methyl-4-methylpentanoic acid 
• 1415986-75-2 (4S)-4-benzyl-3-[(2R)-2-(dibenzylamino)methyl-4-methylpentanoyl]-1,3-oxazolidin-2-one 
• 113543-30-9 (S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one 
• 163810-26-2 (4R)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one 
• 134806-81-8 (4S)-4-isopropyl-3-(4'-methylvaleryl)-2-oxazolidinone 
• 501330-86-5 2-acetyl-4-methyl-pentanoic acid benzyl ester 
• 118053-31-9 benzyl 4-methyl-2-methylenepentanoate 

Downstream Products

• 1018899-99-4 (2R)-2-({[(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl)-4-methylpentanoic acid 
• 210345-69-0 Boc-(R)-β²-HVal-(R)-β²-HAla-(R)-β²-HLeu-(2R,3R)-β^2,3-HAla(α-Me)-(R)-β²-HVal-(R)-β²-HAla-(R)-β²-HLeu-OBn 
• 210345-68-9 (R)-2-[((R)-3-{(R)-2-[((2R,3R)-3-tert-Butoxycarbonylamino-2-methyl-butyrylamino)-methyl]-3-methyl-butyrylamino}-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester 
• 191664-19-4 C₄₆H₇₈N₆O₉ 
• 191664-18-3 (R)-2-({(R)-3-[(R)-2-(tert-Butoxycarbonylamino-methyl)-3-methyl-butyrylamino]-2-methyl-propionylamino}-methyl)-4-methyl-pentanoic acid benzyl ester 
• 191664-17-2 (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester 
• 828254-17-7 2-(R)-(N-boc-aminomethyl) 4-methyl-pentanoic acid 

Relevant academic research and scientific papers

Synthesis and biological evaluation of gramicidin S-inspired cyclic mixed α/β-peptides

Via a Mannich reaction involving a dibenzyliminium species and the titanium enolates of Evans' chiral acylated oxazolidinones the β2-amino acids (R)- and (S)-Fmoc-β2homovaline and (R)-Fmoc- β2homoleucine are synthesized. T

Enantioselective synthesis of beta-amino acids using hexahydrobenzoxazolidinones as chiral auxiliaries

A practical synthetic route for the asymmetric synthesis of β2-amino acids is described. In the first step, the procedure involves the N-acylation of readily available, enantiopure hexahydrobenzoxazolidinone (4R,5R)-1 with 3-methylbutanoyl chloride 2, 4-methylpentanoic acid 3, and 3-(1-tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid 4 to afford derivatives 5a, 5b, and 5c, respectively, which were alkylated with high diastereoselectivity by means of reaction between their sodium enolates and benzyl bromoacetate. Removal of the chiral auxiliary from the alkylated products followed by hydrogenation and hydrolysis gave β2-amino acids (S)-10a, (S)-10b, and (S)-10c, which were N-protected with Fmoc. Enantiomeric (R)-10a-c were similarly prepared from the isomeric hexahydrobenzoxazolidinone (4S,5S)-1; thus, the route presented here provides access to both enantiomers of valuable highly enantioenriched β2-amino acids.

Efficient synthesis of β2-amino acid by homologation of α-amino acids involving the reformatsky reaction and Mannich-type imminium electrophile

Development of new methods for the synthesis of β-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of β2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.

Efficient synthesis of enantiomerically pure β2-amino acids via chiral isoxazolidinones

We report a practical and scalable synthetic route for the preparation of α-substituted β-amino acids (β2-amino acids). Michael addition of a chiral hydroxylamine, derived from α-methylbenzylamine, to an α-alkylacrylate followed by cyclization gives a diastereomeric mixture of α-substituted isoxazolidinones. These diastereomers are separable by column chromatography. Subsequent hydrogenation of the purified isoxazolidinones followed by Fmoc protection affords enantiomerically pure Fmoc-β2-amino acids, which are useful for β-peptide synthesis. This route provides access to both enantiomers of a protected β2-amino acid.

beta-peptides as catalysts: poly-beta-leucine as a catalyst for the Julia-Colonna asymmetric epoxidation of enones.

Poly-beta-leucines have been evaluated as catalysts for the Julia-Colonna asymmetric epoxidation of enones; the beta 3-isomer was found to be an effective catalyst for the epoxidation of chalcone (70% ee) and some analogues.

β2- And β3-Peptides with Proteinaceous Side Chains: Synthesis and Solution Structures of Constitutional Isomers, a Novel Helical Secondary Structure and the Influence of Solvation and Hydrophobic Interactions on Folding

Enantiomerically pure β-amino-acid derivatives with the side chains of Ala, Val, and Leu in the 2- or 3-position (β2- and β3-amino acids, resp.), as well as with substituents in both the 2- and 3-positions (β2,3-amino acids, of like-configuration) have been prepared (compounds 8-17) and incorporated (by stepwise synthesis and fragment coupling, intermediates 24-34) into β-hexa-, β-hepta-, and β-dodecapeptides (1-17). The new and some of the previously prepared β-peptides (35-39) showed NH/ND exchange rates (in MeOH at room temperature) with τ1/2 values of up to 60 days, unrivalled by short chain α-peptides. All β-peptides 1-7 were designed to be able to attain the previously described 31-helical structure (Figs. 1 and 2). CD Measurements (Fig. 4), indicating a new secondary structure of certain β-peptides constructed of β2- and β3-amino acids, were confirmed by detailed NMR solution-structure analyses: a β2-heptapeptide (2c) and a β2,3-hexapeptide (7c) have the 31-helical structure (Figs. 6 and 7), while to a β2/β3-hexapeptide (4) with alternating substitution pattern H-(β2-Xaa-β3-Xaa)3-OH a novel, unusual helical structure (in (D5)pyridine, Fig. 8; and in CD3OH, Figs. 9 and 10) was assigned, with a central ten-membered and two terminal twelve-membered H-bonded rings, and with C=O and N-H bonds pointing alternatively up and down along the axis of the helix (Fig. 11). Thus, for the first time, two types of β-peptide turns have been identified in solution. Hydrophobic interactions of and hindrance to solvent accessibility by the aliphatic side chains are discussed as possible factors influencing the relative stability of the two types of helices.

A practical method for the conversion of β-hydroxy carboxylic acids into the corresponding β-amino acids

Optically active α- or β-substituted βamino acids were synthesized from the corresponding β-hydroxy acids in 4 steps in excellent yield. Stereochemistry was retained at the α-position and reversed at the β-position during the conversion.

Synthesis of a β-hexapeptide from (R)-2-aminomethyl-alkanoic acids and structural investigations

The (R) α-branched β-amino acid derivatives 3-5 with the side chains of alanine, valine and leucine are prepared by amino-methylation of acyloxazolidinones 2a-c and are used for the synthesis of the trifluoroacetate salt 9 of H(-β2-HVal-β2-HAla-β2-HLeu) 2-OH. The CD spectrum of compound 9 is compared with that of the isomer H(-β3-HVal-β3-HAla-β3-HLeu) 2-OH (1) built from the corresponding β-branched β-amino acids.