160801-76-3

Basic information

• Product Name: (2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID
• Synonyms: (2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID
• CAS NO: 160801-76-3
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.17232
• Mol File: 160801-76-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 337 °C at 760 mmHg
• Flash Point: 157.6 °C
• Appearance: /
• Density: 1.185 g/cm³
• Vapor Pressure: 7.39E-06mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: (2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID(160801-76-3)
• EPA Substance Registry System: (2S,3S)-3-AMINO-2-HYDROXYHEXANOIC ACID(160801-76-3)

Safety Data

• Hazardous Substances Data: 160801-76-3(Hazardous Substances Data)

Usage

General Description

(2S,3S)-3-Amino-2-hydroxyhexanoic acid, also known as allo-threonine, is a non-proteinogenic amino acid that contains both an amino group and a hydroxyl group. It is a rare amino acid that is not commonly found in proteins, but it has been identified in some natural products. It is derived from threonine through various enzymatic transformations and is known for its potential use in the pharmaceutical industry as a building block for the synthesis of certain drugs. Its unique structure and properties make it an interesting compound for biochemical and pharmaceutical research.

InChI:InChI=1/C6H13NO3/c1-2-3-4(7)5(8)6(9)10/h4-5,8H,2-3,7H2,1H3,(H,9,10)/t4-,5-/m0/s1

Upstream product

• 117709-02-1 3-propylepoxyethane-2-carboxylic acid methyl ester 
• 13894-63-8 methyl (E)-hex-2-enoate 
• 608520-05-4 (3R,2S)-3-propyloxirane-2-carboxylic acid 
• 92418-71-8 (2R,3R)-2,3-epoxy-1-hexanol 
• 367258-42-2 2-hydroxy-3-nitrohexanoic acid 
• 160801-73-0 (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate 
• 160801-74-1 (2S)-2-(1,1-dimethylethoxycarbonylamino)pentanal 
• 53308-95-5 N-tert-butoxycarbonyl-L-norvaline 
• 364633-42-1 (3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanenitrile 

Downstream Products

• 209398-26-5 (3S)-3-(tert-butoxycarbonylamino)-2-hydroxyhexanoic acid 
• 1166397-39-2 N-cyclopropyl-3-amino-2-hydroxyhexanamide hydrochloride 

Relevant articles and documents

Synthesis method of alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer

The invention relates to a synthesis method of an alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer. The method mainly solves the technical problems that an existing synthesis method uses expensive chiral ligand or highly-toxic raw materials and is not suitable for industrial production. The method includes the steps of firstly, synthesizing substitutive alpha-hydroxyl-beta-amino acid despinner according to a literature method; secondly, stereoscopically and selectively synthesizing an alpha-hydroxyl-beta-amino acid simplex isomer of an (S,S) structure and an alpha-hydroxyl-beta-aminoacid simplex isomer of an (R,R) structure with penicillin G acylase. The method is suitable for preparing the alpha-hydroxyl-beta-amino acid simplex isomers efficiently at low cost.

Discovery of SCH446211 (SCH6): A new ketoamide inhibitor of the HCV NS3 serine protease and HCV subgenomic RNA replication

Introduction of various modified prolines at P2 and optimization of the P1 side chain led to the discovery of SCH6 (24, Table 2), a potent ketoamide inhibitor of the HCV NS3 serine protease. In addition to excellent enzyme potency (Ki* = 3.8 nM), 24 was also found to be a potent inhibitor of HCV subgenomic RNA replication with IC50 and IC90 of 40 and 100 nM, respectively. Recently, antiviral activity of 24 was demonstrated with inhibition of the full-length genotype 2a HCV genome. In addition, 24 was found to restore the responsiveness of the interferon regulatory factor 3 (IRF-3) in cells containing HCV RNA replicons.

Potent 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid-based macrocyclic inhibitors of hepatitis C virus NS3 protease

The NS3 protease of hepatitis C virus (HCV) has emerged as one of the best characterized targets for next-generation HCV therapy. The tetrapeptide 1 and pentapeptide 2 are α-ketoamide-type HCV serine protease inhibitors with modest potency. We envisioned