352-21-6Relevant articles and documents
Synthesis of Enantiomerically Pure γ-Amino-β-hydroxybutyric Acid Using Malic Acid as the Chiral Precursor
Rajashekhar, Betageri,Kaiser, Emil Thomas
, p. 5480 - 5484 (1985)
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
Fuganti, Claudio,Grasselli, Piero,Seneci, P. Fausto,Casati, Paolo
, p. 5275 - 5276 (1986)
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).
A short synthesis of 4-amino-3-hydroxybutyric acid (GABOB) via allyl cyanide
Mete,Maras,Secen
, p. 1879 - 1881 (2003)
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
Xu, Lingjun,Han, Shuwen,Yan, Linjie,Wang, Haifeng,Peng, Haihui,Chen, Fener
supporting information, p. 309 - 317 (2018/02/19)
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.
Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups
Ivsic, Trpimir,Dokli, Irena,Rimac, Ana,Hamersak, Zdenko
, p. 631 - 638 (2014/02/14)
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
Um, Soohyun,Pyee, Yuna,Kim, Eun-Hee,Lee, Sang Kook,Shin, Jongheon,Oh, Dong-Chan
, p. 611 - 622 (2013/05/23)
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.
