4249-19-8

Basic information

• Product Name: S-b-aminoisobutyric acid
• Synonyms: S-b-aminoisobutyric acid;Propanoic acid, 3-aMino-2-Methyl-, (2S)-;(S)-3-AMino-2-Methylpropanoic acid;S-3-Aminoisobutyric acid
• CAS NO: 4249-19-8
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.12
• Mol File: 4249-19-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 179 °C
• Boiling Point: 223.6±23.0 °C(Predicted)
• Appearance: /
• Density: 1.105±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 3.69±0.16(Predicted)
• CAS DataBase Reference: S-b-aminoisobutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: S-b-aminoisobutyric acid(4249-19-8)
• EPA Substance Registry System: S-b-aminoisobutyric acid(4249-19-8)

Safety Data

• Hazardous Substances Data: 4249-19-8(Hazardous Substances Data)

Usage

Description

S-b-aminoisobutyric acid, also known as (+)-α-methyl-β-alanine, is an organic compound that serves as an important reactant in the synthesis of various pharmaceuticals and bioactive molecules. It possesses unique structural features that make it a valuable building block in the development of novel therapeutic agents.

Uses

Used in Pharmaceutical Industry:
S-b-aminoisobutyric acid is used as a key reactant in the chemoenzymatic assembly of cryptophycins, which are potent anticancer therapeutics. These compounds have demonstrated significant antitumor activity against various types of cancer, making them an important class of drugs in the fight against cancer.
In the synthesis of cryptophycins, S-b-aminoisobutyric acid plays a crucial role in the formation of the core structure of these complex natural products. Its unique β-amino acid moiety is essential for the biological activity of cryptophycins, contributing to their potent anticancer properties.
Furthermore, the use of S-b-aminoisobutyric acid in the chemoenzymatic synthesis of cryptophycins allows for the generation of a diverse range of analogs with varying biological activities. This enables researchers to optimize the therapeutic potential of these compounds and develop more effective cancer treatments.
Overall, S-b-aminoisobutyric acid is a valuable component in the development of innovative cancer therapies, with its unique structural features and reactivity playing a pivotal role in the synthesis of potent anticancer agents such as cryptophycins.

Upstream product

• 72342-65-5 (S)-(-)-2-Methylsuccinamic acid 
• 6061-13-8 (2S,3S)-3-methylaspartic acid 
• 174785-09-2 (αS,2S)-N-α-methylbenzyl-3-amino-2-methylpropionic acid 
• 183182-01-6 (2S,5S)-1-Benzoyl-2-tert-butyl-3,5-dimethyl-tetrahydro-pyrimidin-4-one 
• 132696-45-8 (R)-2-{[(tert-butoxycarbonyl)amino]methyl}propionic acid 
• 252579-98-9 (1'R,5S)-1-(1'-phenylethyl)-5-methyldihydropyrimidin-2,4-dione 
• 312613-77-7 (1R,2R)-(+)-pseudoephedrine-β-alanine amide 
• 74-88-4 methyl iodide 
• 351029-66-8 (S)-N-(2'-cyanopropyl)acetamide 
• 7407-59-2 methylbutenedioic acid 
• 190897-47-3 (2S)-3-[(tert-butoxycarbonyl)amino]-2-methylpropanoic acid 
• 382180-28-1 3-amino-2-methyl-N,N-bis-(1-phenyl-ethyl)-propionamide 

Downstream Products

• 1361150-31-3 3-(2,4-dinitro-phenylamino)-2-methyl-propionic acid 
• 203854-58-4 Fmoc-(S)-β(2)hAla-OH 
• 90013-12-0 (R)-2-methyl-1-phenyl-1-pentanone 
• 1671-76-7 p-Methoxyvalerophenon 
• 1009-14-9 phenyl butyl ketone 
• 178977-39-4 (S)-3-[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-2-methyl-propionic acid 

Relevant articles and documents

Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids

We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.

Absolute Configuration and Antibiotic Activity of Piceamycin

The cultivation of a Streptomyces sp. SD53 strain isolated from the gut of the silkworm Bombyx mori produced two macrolactam natural products, piceamycin (1) and bombyxamycin C (2). The planar structures of 1 and 2 were identified by a combination of NMR, MS, and UV spectroscopic analyses. The absolute configurations were assigned based on chemical and chromatographic methods as well as ECD calculations. A new chromatography-based experimental method for determining the configurations of stereogenic centers β to nitrogen atoms in macrolactams was established and successfully applied in this report. These compounds exhibited significant bioactivities against the silkworm entomopathogen Bacillus thuringiensis and various human pathogens as well as human cancer cell lines. In particular, piceamycin potently inhibited Salmonella enterica and Proteus hauseri with MIC values of 0.083 μg/mL and 0.025 μg/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed.

Diastereoselective total synthesis and structural confirmation of surugamide F

Surugamide F is a linear decapeptide (1) isolated along with the cyclic octapeptides surugamides A–E (2–6), from a marine-derived Streptomyces species. The linear peptide 1 is produced by two nonribosomal peptide synthetases (NRPSs) encoded in adjacent open reading frames, which are further flanked by an additional pair of NRPS genes responsible for the biosyntheses of the cyclic peptides 2–6. While the cyclic peptides 2–6 were identified to be cathepsin B inhibitors, the biological activity of the new metabolite 1 still remained unclear. In order to elucidate its unique biosynthetic pathway and biological activity in detail, we planned to develop an efficient synthetic route toward 1. Here we report the diastereoselective total synthesis of 1, utilizing 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase peptide synthesis. During this study, we found that the structural correction of 1 was required, due to the mislabeling of the commercially obtained 3-amino-2-methylpropionic acid, and the true structure of 1 was corroborated by the chemical synthesis and chromatographic comparison.