118125-41-0

Basic information

• Product Name: Z-4-AMINO-3-HYDROXYBUTYRIC ACID
• Synonyms: Z-4-AMINO-3-HYDROXYBUTYRIC ACID;Z-GABOB-OH;Z-DL-4-amino-3-hydroxybutyric acid
• CAS NO: 118125-41-0
• Molecular Formula: C12H15NO5
• Molecular Weight: 253.25
• Mol File: 118125-41-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Z-4-AMINO-3-HYDROXYBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: Z-4-AMINO-3-HYDROXYBUTYRIC ACID(118125-41-0)
• EPA Substance Registry System: Z-4-AMINO-3-HYDROXYBUTYRIC ACID(118125-41-0)

Safety Data

• Hazardous Substances Data: 118125-41-0(Hazardous Substances Data)

Upstream product

• 924-49-2 DL-4-amino-3-hydroxybutyric acid 
• 501-53-1 benzyl chloroformate 
• 119960-08-6 N-Cbz-GABOB methyl ester 
• 100-51-6 benzyl alcohol 
• 82961-77-1 methyl 4-<(benzyloxycarbonyl)amino>-3-oxobutanoate 
• 87554-49-2 (R)-(-)-methyl N-t-butyloxycarbonyl-3-hydroxy-4-aminobutanoate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 119960-04-2 methyl 4-[(tert-butoxycarbonyl)amino]-3-oxobutanoate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 7013-07-2 (R)-4-Amino-3-hydroxybutanoic acid 
• 121505-94-0 N-benzyloxycarbonyl-glycine-N'-methoxy-N'-methylamide 
• 67561-03-9 N-benzyloxycarbonylglycinal 
• 126832-13-1 (1'S)-4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 2'-hydroxy-1',2',2'-triphenylethyl ester 
• 126832-13-1 (1'R)-4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 2'-hydroxy-1',2',2'-triphenylethyl ester 

Downstream Products

• 161971-54-6 methyl (RS)-<4-(benzyloxycarbonyl)amino>-3-hydroxybutyrate 
• 157542-04-6 (RS)-<1-(benzyloxycarbonyl)amino>-butan-2,4-diol 
• 160246-03-7 N-Benzyloxycarbonyl-4-amino-3-benzyloxybutyric acid 
• 160246-02-6 p-Nitrobenzyl (N-benzyloxycarbonyl-4-amino-3-benzyloxy)butyrate 
• 160246-04-8 Octyl 2,3,4-tri-O-benzyl-6-O-(N-benzyloxycarbonyl-4'-amino-3'-benzyloxybutyryl)-β-D-glucopyranoside 
• 7013-07-2 (R)-4-Amino-3-hydroxybutanoic acid 

Relevant articles and documents

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.

A Facile Synthesis of (R)-4-Amino-3-hydroxybutanoic Acid (GABOB) from 3-Hydroxypyridine

(R)-4-Amino-3-hydroxybutanoic acid (GABOB) has been synthesized facilely from 3-hydroxypyridine via 1-carbobenzoxy-1,2,3,4-tetrahydro-3-hydroxypyridine employing lipase-mediated kinetic resolution.

SYNTHESIS OF OCTYL β-D-GLUCOPYRANOSIDE-AMINOBUTYRIC (GABA) AND AMINOHYDROXYBUTYRIC (GABOB) CONJUGATES

The syntheses of octyl β-D-glucopyranoside-GABA and GABOB conjugates are presented.The selectively protected octyl-β-D-glucopyranoside and γ-aminobutyric acids, were coupled with N,N'-dicyclohexylcarbodiimide. 1H and 13C NMR spectroscopy were used to verify the proposed structures.

Absolute configuration of main chain of AAL-toxins

AAL-toxins TA1 1 and TA2 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1,3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthetic samples by comparison of their 500 MHz 1H-NMR spectra. The remaining stereocenters were determined by the comparison of 1H-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.

Baker's yeast reduction of N-protected methyl 4-amino-3-oxobutanoates and 3-oxopentanoates

Baker's yeast reduction of N-tert-butoxycarbonyl (Boc) or N-benzyloxycarbonyl (Cbz) protected methyl 4-amino-3-oxopentanoates 4b-e and 4-amino-3-oxobutanoates 7a,b stereoselectively afforded the erythro-hydroxy esters 5b-e and (R)-hydroxy esters 8a,b, res

Simple Three-Step Synthesis of (R)- and (S)-4-Amino-3-hydroxybutanoic Acid (GABOB) by Stereoselective Aldol Addition

A simple synthesis of both (R)- and (S)-GABOB (5) is reported.In the key step, doubly deprotonated (R)- or (S)-2-Hydroxy-1,2,2-triphenylethyl acetate (HYTRA) (1) is added to Cbz-protected glycinal (2).