5891-45-2

Basic information

• Product Name: Z-GLU-OTBU
• Synonyms: Z-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER;Z-GLU-OTBU;Z-GLUTAMIC ACID-OTBU;Z-GLUTAMIC ACID TERT-BUTYL ESTER;N-ALPHA-CARBOBENZOXY-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER;Z-L-glutamic acid α-tert.butyl ester;N-CBZ-L-glutamicacidbenzylesterR-t-butylester;N-S-CBZ-L-GLUTAMIC ACID S-BENZYL ESTER R-TERT-BUTYL ESTER
• CAS NO: 5891-45-2
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.37
• EINECS: 2017-001-1
• Product Categories: Z-Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 5891-45-2.mol

Chemical Properties

• Melting Point: 81.0 to 85.0 °C
• Boiling Point: 522.6 °C at 760 mmHg
• Flash Point: 269.9 °C
• Appearance: /Solid
• Density: 1.197 g/cm³
• Vapor Pressure: 9.49E-12mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: 2-8°C
• PKA: 4.48±0.10(Predicted)
• CAS DataBase Reference: Z-GLU-OTBU(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLU-OTBU(5891-45-2)
• EPA Substance Registry System: Z-GLU-OTBU(5891-45-2)

Safety Data

• Hazardous Substances Data: 5891-45-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

A protected glutamic acid for use in peptide synthesis.

InChI:InChI=1/C17H23NO6/c1-17(2,3)24-15(21)13(9-10-14(19)20)18-16(22)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,19,20)/t13-/m0/s1

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 57732-63-5 1-tert-butyl 5-methyl (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioate 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 56-86-0 L-glutamic acid 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 203919-89-5 (S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 32159-21-0 Cbz-L-pGlu-OH 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 100-51-6 benzyl alcohol 
• 125134-29-4 (R)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 97261-93-3 N-(N-benzyloxycarbonyl-L-γ-glutamyl)-glycine 
• 103673-94-5 N-(N-Benzyloxycarbonyl-L-γ-glutamyl-1-tert.-butylester)-glycin-tert.-butylester 
• 104979-31-9 N-(N-Benzyloxycarbonyl-L-γ-glutamyl-1-tert-butylester)-S-benzyl-cystein-methylester 
• 103777-98-6 N-(N-Benzyloxycarbonyl-L-γ-glutamyl-1-tert.-butylester)-L-asparaginsaeure-di-tert.-butylester 
• 141334-69-2 (S)-2-Benzyloxycarbonylamino-4-(2-hydroxy-octylcarbamoyl)-butyric acid tert-butyl ester 
• 135912-91-3 (S)-2-Benzyloxycarbonylamino-4-(2-hydroxy-hexylcarbamoyl)-butyric acid tert-butyl ester 
• 23736-78-9 N-(benzyloxycarbonyl)-γ-L-glutamyl-L-glutamic acid, α,α'-di-tert-butyl γ-methyl triester 
• 32719-56-5 tri-tert-butyl N--L-glutamate 
• 32719-57-6 tetra-tert-butyl N--L-γ-glutamyl>-L-glutamate 
• 32816-47-0 penta-tert-butyl N--L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate 
• 32719-58-7 hexa-tert-butyl N--L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate 
• 105664-18-4 Z-Glu-OtBu 
• 135913-03-0 (S)-2-Benzyloxycarbonylamino-4-((R)-2-hydroxy-3-morpholin-4-yl-propylcarbamoyl)-butyric acid tert-butyl ester 
• 91921-47-0 N-Benzyloxycarbonyl-γ-(S)-glutamyl(α-tert.-butylester)-γ-(S)-glutamyl(α-tert.-butylester)-(S)-prolin-tert.-butylester 

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N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23percent yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid.Reduction of 6 to 7 and treatment with N-(trichloroethoxy)carbonyl>-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g).Following α-amino and α-carboxyl deprotections of 11 and 12, EEDQ mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36).The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5).These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

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