85995-53-5

Basic information

• Product Name: 2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID
• Synonyms: 2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID;CARBOBENZYLOXY-DL-THREONINE;Cbz-Allo-Thr-OH
• CAS NO: 85995-53-5
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.25
• Mol File: 85995-53-5.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID(85995-53-5)
• EPA Substance Registry System: 2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID(85995-53-5)

Safety Data

• Hazardous Substances Data: 85995-53-5(Hazardous Substances Data)

Usage

Description

2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID, also known as Z-3-HB-OH, is a serine derivative with a benzyl group attached to the hydroxyl group and a carbamate group on the amino group. It is a compound used in the synthesis of peptides and proteins, playing a crucial role in biochemistry and pharmaceutical research.
Used in Biochemistry and Pharmaceutical Research:
2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID is used as a protecting group for the hydroxyl group of serine during peptide synthesis, ensuring the stability and proper formation of peptide bonds.
Used in Peptide and Protein Synthesis:
2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID is used as a building block for the construction of peptide and protein structures, facilitating the development of novel therapeutic agents and bioactive molecules.
Used in Drug Delivery Systems:
2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID is used as a component in the design of drug delivery systems, potentially enhancing the targeted delivery and therapeutic efficacy of peptide and protein-based drugs.
Used in Targeted Therapies:
2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-BUTYRIC ACID is used in the development of targeted therapies, where its incorporation into peptide and protein structures can aid in the specific recognition and treatment of diseased cells or tissues.

Upstream product

• 28954-12-3 (2S,3S)-2-amino-3-hydroxybutanoic acid 
• 501-53-1 benzyl chloroformate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 72-19-5 rac-allo-threonine 
• 632-20-2 D-Threonine 
• 80-68-2 DL-threonine 
• 72-19-5 L-threonine 
• 72-19-5 D-threonine 

Downstream Products

• 101890-79-3 2-benzyloxycarbonylamino-acetoacetic acid benzyl ester 
• 16597-50-5 2-benzyloxycarbonylamino-3-hydroxy-butyric acid benzyl ester 
• 98777-34-5 (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 

Relevant articles and documents

Intramolecular Amidoalkylation of Chiral Imines and Iminium Ions: Stereoselective Synthesis of anti-1,2- and -1,3-Aminoalcohols

When treated with Lewis acids, 2- or 3-vinyl- or -phenylsiloxyaminoacetals generated the corresponding imines or iminium ions which in turn underwent smooth intramolecular amidoalkylation to afford anti-1,2- or -1,3-aminoalcohol derivatives in very high c

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

BENZIMIDAZOLE DERIVATIVES AS BROMODOMAIN INHIBITORS

Compounds of formula (I) and salts thereof: wherein R1, R2, R3, R4 are defined herein. Compounds of formula (I) and salts thereof have been found to inhibit the binding of the BET family of bromodomain proteins to, for example, acetylated lysine residues and thus may have use in therapy, for example in the treatment of autoimmune and inflammatory diseases, such as rheumatoid arthritis; and cancers.