80384-27-6

Basic information

• Product Name: Z-D-THR-OH
• Synonyms: N-Benzyloxycarbonyl-D-threonine~Z-D-Thr-OH;N-Benzyloxycarbonyl-D-threonine, 98+%;Z-D-THREONINE extrapure;(2R,3S)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid;Cbz-D-threonine;N-Cbz-D-threonine Z-D-Thr-OH;Z-D-threonine≥ 98% (HPLC);CBZ-D-THR-OH
• CAS NO: 80384-27-6
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.25
• Mol File: 80384-27-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 100-102°C
• Boiling Point: 483.7 °C at 760 mmHg
• Flash Point: 246.3 °C
• Appearance: /
• Density: 1.309 g/cm³
• Vapor Pressure: 3.62E-10mmHg at 25°C
• Refractive Index: 5 ° (C=2, AcOH)
• Storage Temp.: Store at RT.
• PKA: 3.58±0.10(Predicted)
• BRN: 4695777
• CAS DataBase Reference: Z-D-THR-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-THR-OH(80384-27-6)
• EPA Substance Registry System: Z-D-THR-OH(80384-27-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 80384-27-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N-Cbz-D-threonine is an N-Cbz-protected form of D-Threonine (T405525). D-Threonine is the unnatural isomer of L-Threonine (T405500) and is known to inhibit growth and cell wall synthesis of Mycobacterium smegmatis. D-Threonine is also used as a synthetic intermediate for the production of chiral antibiotics.

InChI:InChI=1/C12H15NO5/c1-8(14)10(11(15)16)13-12(17)18-7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,17)(H,15,16)/t8?,10-/m1/s1

Upstream product

• 632-20-2 D-Threonine 
• 501-53-1 benzyl chloroformate 
• 72-19-5 rac-allo-threonine 
• 80-68-2 DL-threonine 
• 72-19-5 D-threonine 

Downstream Products

• 162553-97-1 N-Cbz-D-Threonyl-L-alanine tert-butyl ester 
• 1402887-65-3 C₁₅H₁₉NO₅ 
• 1402887-66-4 C₂₁H₃₃NO₅Si 
• 1402887-64-2 C₁₄H₂₀N₂O₅ 
• 57224-63-2 methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 
• 122871-70-9 (4R,5S)-5-methyl-2-oxooxazolidine-4-carboxylic acid 
• 80582-05-4 (3R,4R)-3-(benzyloxycarbonylamino)-4-methyl-azetidin-2-one 
• 16597-50-5 2-benzyloxycarbonylamino-3-hydroxy-butyric acid benzyl ester 
• 101890-79-3 2-benzyloxycarbonylamino-acetoacetic acid benzyl ester 
• 1374666-79-1 (2S,3R)-2-methyl-4-oxo-3-oxetanylcarbamic acid benzyl ester 
• 1280627-27-1 5-bromopentanoic acid (2R)-2-benzyloxycarbonylamino-2-[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-(S)-1-methyl-ethyl ester 
• 1280627-25-9 (2S)-2-hydroxy-(1R)-{[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-propyl}-carbamic acid benzyl ester 
• 1280627-33-9 1-(4-{2-benzyloxycarbonylamino-(2S)-2-[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-(1R)-1-methyl-ethoxycarbonyl}-butyl)-3-methyl-3H-imidazol-1-ium bromide 
• 85995-50-2 N-Z-D-threonine benzyl ester 

Relevant articles and documents

EP300/CREBBP INHIBITOR

The present invention provides a compound having excellent histone acetyltransferase inhibitory activity against EP300 and/or CREBBP, or a pharmacologically acceptable salt thereof. The compound is represented by the following formula (1) or a pharmacologically acceptable salt thereof: wherein ring Q1, ring Q2, R1, R2, R3 and R4 respectively have the same meanings as defined in the specification.

N -(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: Synthesis and structure-activity and structure-property relationships

The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure-activity and structure-property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC50 = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.

Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative

In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs. 2009 American Chemical Society.