97363-14-9

Basic information

• Product Name: (R)-3-hydroxybutyrate thiophenyl ester
• Synonyms: (R)-3-hydroxybutyrate thiophenyl ester
• CAS NO: 97363-14-9
• Molecular Weight: 196.27
• Mol File: 97363-14-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-3-hydroxybutyrate thiophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-hydroxybutyrate thiophenyl ester(97363-14-9)
• EPA Substance Registry System: (R)-3-hydroxybutyrate thiophenyl ester(97363-14-9)

Safety Data

• Hazardous Substances Data: 97363-14-9(Hazardous Substances Data)

Upstream product

• 625-72-9 (R)-3-hydroxybutyric acid 
• 108-98-5 thiophenol 
• 108070-88-8 3-(tert-butyldimethylsilyl) butyrate thiophenyl ester 

Downstream Products

• 97381-27-6 3-Benzylamino-5-benzyloxy-2-((R)-1-hydroxy-ethyl)-pentanethioic acid S-phenyl ester 
• 121651-93-2 S-Phenyl (2S,3S)-2-<(1R)-hydroxyethyl)>-3-N-p-methoxybenzylamino-5-trimethylsilyl-4-pentynethioate 
• 105662-87-1 (3S,4S)-4-Ethynyl-3-<(1R)-hydroxyethyl>-N-p-methoxybenzyl-2-azetidinone 

Relevant articles and documents

Cysteine-Aminoethylation-Assisted Chemical Ubiquitination of Recombinant Histones

Histone ubiquitination affects the structure and function of nucleosomes through tightly regulated dynamic reversible processes. The efficient preparation of ubiquitinated histones and their analogs is important for biochemical and biophysical studies on histone ubiquitination. Here, we report the CAACU (cysteine-aminoethylation assisted chemical ubiquitination) strategy for the efficient synthesis of ubiquitinated histone analogs. The key step in the CAACU strategy is the installation of an N-alkylated 2-bromoethylamine derivative into a recombinant histone through cysteine aminoethylation, followed by native chemical ligation assisted by Seitz's auxiliary to produce mono- and diubiquitin (Ub) and small ubiquitin-like modifier (SUMO) modified histone analogs. This approach enables the rapid production of modified histones from recombinant proteins at about 1.5-6 mg/L expression. The thioether-containing isopeptide bonds in the products are chemically stable and bear only one atomic substitution in the structure, compared to their native counterparts. The ubiquitinated histone analogs prepared by CAACU can be readily reconstituted into nucleosomes and selectively recognized by relevant interacting proteins. The thioether-containing isopeptide bonds can also be recognized and hydrolyzed by deubiquitinases (DUBs). Cryo-electron microscopy (cryo-EM) of the nucleosome containing H2BKC34Ub indicated that the obtained CAACU histones were of good quality for structural studies. Collectively, this work exemplifies the utility of the CAACU strategy for the simple and efficient production of homogeneous ubiquitinated and SUMOylated histones for biochemical and biophysical studies.

Stereocontrolled synthesis of (+)-thienamycin from 3(R)-hydroxybutyric acid

The vinyloxyborane(5), prepared from (+)-S-phenyl-3(R)-butanethioate, 9-BBN triflate and diisopropylethylamine, reacted with N-(3-benzyloxypropylidene)benzylamine to give the β-benzylamino thiol ester(6) in a moderate yield, which was efficiently converted to the optically pure thienamycin intermediate(10).