352-21-6

Usage

Purification Methods

Purify GABOB through a Dowex 50Wx8 resin, eluting with 1.3N NH4OH, evaporating and crystallising the residue by dissolving it in H2O and adding EtOH. It is an anticonvulsant. [Renaud & Seebach Synthesis 424 1986, Takano et al. Tetrahedron Lett 29 795 1988, Beilstein 4 IV 3187.]

InChI:InChI=1/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/p-1

Upstream product

• 83349-20-6 4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 
• 109462-43-3 3,4 epoxybutyric acid 
• 95574-97-3 (R)-(-)-4-chloro-3-hydroxybutanoic acid 
• 111607-76-2 acide (S)-benzamido-4 hydroxy-3 butanoique 
• 175158-38-0 (S)-4-chloro-3-hydroxybutanamide 
• 1431373-89-5 (S)-4-(benzyl-benzyloxycarbonyl-amino)-3-benzyloxy-butyric acid 
• 1607830-40-9 (S)-3-(benzyloxy)-4-(benzyloxycarbonylamino)butyric acid 
• 22677-21-0 (R)-4-hydroxy-2-pyrrolidinone 
• 104768-72-1 (R)-4-Azido-3-hydroxybutanoic acid 
• 1093216-34-2 (3R)-3-acetoxy-4-(N-tert-butoxycarbonyl-N-formylamino)butyric acid 
• 1093216-44-4 (3R)-4-(N-tert-butoxycarbonyl-N-formylamino)-3-(tert-butyldimethylsilyloxy)butyric acid 
• 1417995-87-9 thalassospiramide D 
• 56-12-2 4-amino-n-butyric acid 
• 74889-64-8 (DL)-4-amino-3-hydroxybutanenitrile hydrochloride 

Downstream Products

• 111607-77-3 (S)-hydroxy-4 phenylacetyl-1 pyrrolidinone-2 
• 99211-78-6 (S)-4-Dimethylamino-3-hydroxy-butyric acid 
• 1455087-62-3 (S)-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-3-hydroxybutanoic acid 
• 2921-13-3 (R)-4-dimethylamino-3-hydroxybutanoic acid 
• 7010-89-1 3-Hydroxy-4-guanidino-buttersaeure 
• 38090-53-8 trans-4-aminocrotonic acid 
• 461-06-3 CARNITINE 
• 542-06-3 (+/-)-4-Dimethylamino-3-hydroxy-buttersaeure 
• 409341-03-3 tert-butyl 4-hydroxy-2-oxopyrrolidine-1-carboxylate 
• 22677-21-0 4-hydroxy-2-oxopyrrolidine 
• 68252-20-0 4-Trimethylsilyloxy-1H-pyrrolidin-2one 
• 157542-04-6 (RS)-<1-(benzyloxycarbonyl)amino>-butan-2,4-diol 
• 80503-94-2 (R)-4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 
• 127852-78-2 (S)-4-((tert-butoxycarbonyl)amino)-3-hydroxybutanoic acid 

Relevant academic research and scientific papers

Synthesis of Enantiomerically Pure γ-Amino-β-hydroxybutyric Acid Using Malic Acid as the Chiral Precursor

The synthesis of enantiomerically pure γ-amino-β-hydroxybutyric acid using malic acid as the chiral precursor is described.The key step involves the regioselective carboxamidation of the β-carboxyl group (adjacent to the hydroxyl) in malic acid.This was achieved by converting (S)-malic acid to its cyclic anhydride 8, which was then treated with ammonia.Protection of the alcoholic group in the ester amide 9 as a tert-butyl ether followed by LiAlH4 reduction gave 3-(tert-butyloxy)-4-aminobutanol (11c).The amino group in 11c was protected as the tert-butyl carbamate to give (S)-3-(tert-butyloxy)-4-butanol (12c).The oxidation of the primary alcoholic group was successfully carried out with zinc permanganate to give the desired acid (S)-3-(tert-butyloxy)-4-butyric acid (13c).Removal of the protecting groups gave (S)-(+)-γ-amino-β-hydroxybutyric acid, the optical rotation measurements of which indicated no racemization during the six-step synthesis.The R isomer could be synthesized starting from (R)-malic acid.Thus a short and efficient route to chirally pure (R)- and (S)-γ-amino-β-hydroxybutyric acid is presented.Furthermore, this work also highlights zinc permanganate as a useful oxidant for the preparation of carboxylic acids.

FURTHER INFORMATION ON THE STERIC COURSE OF THE BAKER'S YEAST REDUCTION OF 4-SUBSTITUTED-3-OXOBUTANOATES

Yeast reduction of (6), (7), (8), (12) and (13) affords (3R)(9) and (3R)(10) of high optical purity, racemic (11), and (3S)(14) and (3S)(15).

An efficient transformation of cyclic ene-carbamates into ω-(N-formylamino)carboxylic acids by ruthenium tetroxide oxidation

The ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon-carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates der

A short synthesis of 4-amino-3-hydroxybutyric acid (GABOB) via allyl cyanide

4-Amino-3-hydroxybutyric acid was synthesized from allyl cyanide in four steps in an overall yield of 38%. Ultrasonically promoted epoxidation of allyl cyanide with m-chloroperoxybenzoic acid giving oxiranylacetonitrile was used as a key step.

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

Design, synthesis, and biological evaluation of simplified side chain hybrids of the potent actin binding polyketides rhizopodin and bistramide

The natural products rhizopodin and bistramide belong to an elite class of highly potent actin binding agents. They show powerful antiproliferative activities against a range of tumor cell lines, with IC50 values in the low-nanomolar range. At the molecular level they disrupt the actin cytoskeleton by binding specifically to a few critical sites of G-actin, resulting in actin filament stabilization. The important biological properties of rhizopodin and bistramide, coupled with their unique and intriguing molecular architectures, render them attractive compounds for further development. However, this is severely hampered by the structural complexity of these metabolites. We initiated an interdisciplinary approach at the interface between molecular modeling, organic synthesis, and chemical biology to support further biological applications. We also wanted to expand structure-activity relationship studies with the goal of accessing simplified analogues with potent biological properties. We report computational analyses of actin-inhibitor interactions involving molecular docking, validated on known actin binding ligands, that show a close match between the crystal and modeled structures. Based on these results, the ligand shape was simplified, and more readily accessible rhizopodin-bistramide mimetics were designed. A flexible and modular strategy was applied for the synthesis of these compounds, enabling diverse access to dramatically simplified rhizopodin-bistramide hybrids. This novel analogue class was analyzed for its antiproliferative and actin binding properties.

Synthesis of GABOB and GABOB-Based Chiral Units Possessing Distinct Protecting Groups

In addition to the varied biological activity of GABOB (4-amino-3-hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee.

Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups

In addition to the varied biological activity of GABOB (4-amino-3- hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee. A stereoselective route to GABOB (4-amino-3-hydroxybutanoic acid) derivatives with three different protecting groups is presented. Selective deprotection produced diprotected chiral building blocks with a free carboxylic acid or hydroxy group. Removal of all the protecting groups allowed GABOB to be isolated. Copyright

Thalassospiramide G, a new γ-amino-acid-bearing peptide from the marine bacterium Thalassospira sp

In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2-3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy- penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H-1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2-3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.

Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide

Synthetic routes to (S)-oxiracetam and (S)-GABOB have been developed starting from (R)-glyceraldehyde acetonide through its conversion to an appropriate aldehyde intermediate followed by reductive amination using glycinamide hydrochloride/benzyl amine and subsequent chemical transformations.