60686-50-2

Basic information

• Product Name: Z-L-GLA(OTBU)2-OH
• Synonyms: N-alpha-(Benzyloxycabonyl)-gamma-carboxy-L-glutamic-acid-gamma-di-t-butylester;N-ALPHA-(BENZYLOXYCARBONYL)--CARBOXY-L-GLUTAMIC-ACID--DI-T-BUTYL ESTER;Z-g-carboxy-Glu(OtBu)2-OH;Z-γ-carboxy-γ-(di-tert-butyl ester)-L-glutamic acid;Z-γ-carboxy-L-Glu(OtBu)2-OH;Z-γ-carboxy-γ-(di-tert-butyl ester)-L-glutamic acid99%;N-ALPHA-(BENZYLOXYCARBONYL)-GAMMA-CARBOXY-L-GLUTAMIC-ACID-GAMMA-DI-T-BUTYL ESTER;N-ALPHA-(BENZYLOXYCARBONYL)-GAMMA-CARBOXY-L-GLUTAMIC-ACID-GAMMA-DI-TERT-BUTYL ESTER
• CAS NO: 60686-50-2
• Molecular Formula: C₂₂H₃₁NO₈
• Molecular Weight: 437.48
• Product Categories: amino acids
• Mol File: 60686-50-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-L-GLA(OTBU)2-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-L-GLA(OTBU)2-OH(60686-50-2)
• EPA Substance Registry System: Z-L-GLA(OTBU)2-OH(60686-50-2)

Safety Data

• Hazardous Substances Data: 60686-50-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Z-L-GLA(OTBU)2-OH is used as a chiral ligand in asymmetric synthesis for the creation of enantiomerically pure compounds. Its Z-Ligand configuration allows for the selective formation of specific enantiomers, which is crucial in the production of pharmaceuticals and other chiral molecules where stereochemistry plays a significant role in biological activity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Z-L-GLA(OTBU)2-OH is utilized as a building block for the synthesis of complex molecules with specific stereochemical properties. The presence of the hydroxyl group and the protective tert-butyl ester group allows for the controlled formation of target molecules with desired biological activities and selectivity.
Used in Research and Development:
Z-L-GLA(OTBU)2-OH is also used in research and development for the study of asymmetric synthesis and the development of new synthetic methods. Its unique structure and properties make it a valuable tool for exploring the mechanisms of enantioselective reactions and for designing novel catalysts and reagents.

Upstream product

• 1492-52-0 methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate 
• 541-16-2 t-butyl malonate 
• 133464-36-5 (S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 133464-37-6 (4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 912354-29-1 (4S)-2-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethyl)malonic acid di-tert-butyl ester 
• 873310-64-6 2S-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethylene)-malonic acid di-tert-butyl ester 
• 912354-37-1 (2S)-2-(2-benzyloxycarbonylamino-3-hydroxypropyl)malonic acid di-tert-butyl ester 
• 56877-40-8 Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester 
• 56877-43-1 Z-DL-Gla(OtBu)2-OH 

Downstream Products

• 53861-57-7 γ-carboxy-L-glutamic acid 
• 80954-40-1 N-(benzyloxycarbonyl)-L-γ-carboxyglutamyl-L-alanyl-L-leucine benzyl ester 
• 80954-42-3 N-(benzyloxycarbonyl)-L-γ-methyleneglutamyl-L-alanyl-L-leucine benzyl ester 
• 87136-44-5 N-Benzyloxycarbonyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-L-arginyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamic Acid α-Methyl Ester Acetate Salt 
• 87136-47-8 γ,γ-Di-tert-butyl-L-γ-carboxyglutamyl-L-arginyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamic Acid α-Methyl Ester p-Toluenesulfonate Salt 
• 87136-51-4 N-Benzyloxycarbonyl-L-γ-carboxyglutamyl-L-arginyl-L-γ-carboxyglutamic Acid α-Methyl Ester Trifluoroacetate Salt 
• 87173-10-2 γ,γ-Di-tert-butyl-L-γ-carboxyglutamic Acid α-Methyl Ester p-Toluenesulfonate Salt 
• 87136-42-3 N-Benzyloxycarbonyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-L-arginine 
• 74201-27-7 L-phenylalanyl-L-leucyl-L-γ-carboxyglutamyl-L-glutamyl-L-leucine methyl ester trifluoroacetate salt 
• 74193-70-7 N-tert-butyloxycarbonyl-L-phenylalanyl-L-leucyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-γ-tert-butyl-L-glutamyl-L-leucine methyl ester 
• 74193-66-1 N-benzyloxycarbonyl-L-γ-carboxyglutamyl-L-serine methyl ester 
• 93254-99-0 N-(benzyloxycarbonyl)-L-γ-carboxyglutamic acid, α-phenyl ester 
• 93255-00-6 N-(benzyloxycarbonyl)-L-γ-methyleneglutamic acid, α-phenyl ester 
• 111662-65-8 N-α-(9-fluorenylmethoxycarbonyl)-L-γ-carboxy-glutamic acid-γ,γ-tert-butyl ester 

Relevant articles and documents

Design and concise synthesis of fully protected analogues of L-γ-carboxyglutamic acid

The design and synthesis of four nonnaturally occurring amino acid analogues of L-γ-carboxyglutamic acid (Gla), appropriately protected for Fmoc-based solid-phase peptide synthesis (SPPS), is described. These amino acids are Bu-Mal 2, BCAH 3, Pen-Mal 4, a

The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides

Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues. The Royal Society of Chemistry 2000.