24277-39-2

Basic information

• Product Name: Boc-L-glutamic acid 1-tert-butyl ester
• Synonyms: N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER;N-ALPHA-T-BOC-L-GLU-ALPHA-T-BUTYL ESTER;N-ALPHA-T-BOC-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-GLUTAMIC ACID-ALPHA-TERT-BUTYL ESTER;N-T-BUTOXYCARBONYL-L-GLUTAMIC ACID 1-T-BUTYL ESTER;N-T-BOC-L-GLUTAMIC ACID ALPHA-T-BUTYL ESTER;N-TERT-BUTOXYCARBONYL-L-GLUTAMIC ACID 1-TERT-BUTYL ESTER;N-T-boc-L-glutamic acid A-T-butyl-ester
• CAS NO: 24277-39-2
• Molecular Formula: C₁₄H₂₅NO₆
• Molecular Weight: 303.35
• Product Categories: Amino Acids;Glutamic acid [Glu, E];Boc-Amino Acids and Derivative
• Mol File: 24277-39-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 111.0 to 115.0 °C
• Boiling Point: 449.8 °C at 760 mmHg
• Flash Point: 225.8 °C
• Appearance: white powder
• Density: 1.121 g/cm³
• Vapor Pressure: 2.42E-09mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: −20°C
• Solubility: Soluble in dimethyl formamide.
• PKA: 4.48±0.10(Predicted)
• BRN: 3653769
• CAS DataBase Reference: Boc-L-glutamic acid 1-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-glutamic acid 1-tert-butyl ester(24277-39-2)
• EPA Substance Registry System: Boc-L-glutamic acid 1-tert-butyl ester(24277-39-2)

Safety Data

• Statements: 22/22-36/37/38
• Safety Statements: 4-7-28-35-44
• WGK Germany: 3
• Hazardous Substances Data: 24277-39-2(Hazardous Substances Data)

Usage

Uses

Boc-Glu-OtBu is an N-terminal protected amino acid used in solid-phase peptide synthesis (SPPS) to make unique peptides containing glutamate tert-butyl ester residues.

InChI:InChI=1/C14H25NO6/c1-13(2,3)20-11(18)9(7-8-10(16)17)15-12(19)21-14(4,5)6/h9H,7-8H2,1-6H3,(H,15,19)(H,16,17)/t9-/m0/s1

Upstream product

• 28812-54-6 α-tert-butyl γ-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamate 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 24277-38-1 (S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 611182-62-8 N-(diphenylmethylene)-L-glutamic acid 1-(1,1-dimethylethyl) 5-benzyl ester 
• 28812-54-6 N-tert-butoxyxarbonyl-L-glutamic acid γ-benzyl α-tert-butyl diester 
• 1676-73-9 glutamic acid γ-benzyl ester 
• 80165-23-7 2-Amino-pentanedioic acid 5-benzyl ester 1-tert-butyl ester 
• 45120-30-7 L-glutamic acid α-tert-butyl ester 
• 540-88-5 acetic acid tert-butyl ester 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 138-15-8 l-glutamic acid hydrochloride 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 3077-51-8 γ-methyl L-glutamate hydrochloride 

Downstream Products

• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 2387-23-7 1,3-Dicyclohexylurea 
• 189380-79-8 4-(2-hydroxyethylthioethyl)-L-glutamate 
• 284043-05-6 γ-O-(4-hydroxy-3-methoxyphenacetyl) t-butyl N-t-boc L-glutamate 
• 618095-50-4 N^α-(tert-butoxycarbonyl)-γ-(6-nitroveratryl)glutamic acid tert-butyl ester 
• 916054-62-1 2-tert-butoxycarbonylamino-4-[1-(tert-butoxycarbonylmethyl-carbamoyl)-3-methoxycarbonyl-propylcarbamoyl]-butyric acid tert-butyl ester 
• 680612-90-2 1-tert-butyl 5-[4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenyl] N-(tert-butoxycarbonyl)-L-glutamate 
• 1111628-63-7 2,7-bis{3-[1-[(4S)-4-(tert-butoxycarbonyl)-4-(tert-butoxycarbonylamino)butanoyloxy]prop-2-yl]-4-nitrostyryl}-9,9-bis(3,6-dioxa-1-heptyl)fluorene 
• 1111628-57-9 4,4'-bis{3-[1-[(4S)-4-(tert-butoxycarbonyl)-4-(tert-butoxycarbonylamino)butanoyloxy]prop-2-yl]-4-nitrostyryl}-3,3'-dimethoxybiphenyl 
• 1221686-65-2 (S)-2-tert-butoxycarbonylamino-4-(3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylcarbamoyl)-butyric acid tert-butyl ester 
• 2643-69-8 3-(L-γ-glutamylamino)benzoic acid 
• 1336933-94-8 C₂₃H₃₄N₂O₇ 
• 1220125-16-5 N⁵-(3-chloro-4-methyl-5-sulfophenyl)-L-glutamine 
• 1220125-05-2 (2S)-2-amino-4-[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]butanoic acid 

Relevant articles and documents

Synthesis of novel carboranyl derivatives of α-amino acids

New routes to closo-carboranyl derivatives of L-lysine and L-glutamic acid with free α-NH2 groups were proposed.

Synthesis and photochemical reactivity of caged glutamates with a π-extended coumarin chromophore as a photolabile protecting group

'Caging' and 'uncaging' bioactive substrates are key techniques in studying a wide variety of biological processes. In the present study, two-types of novel caged glutamates with a two-photon absorption (TPA) core, that is, π-extended coumarin, were synthesized and their photochemical release of glutamate was analyzed. The high yields of glutamate (>92%) were observed in the photolysis of compounds 1 and 10, respectively.

Synthesis of ortho-carboranyl derivatives of (S)-asparagine and (S)-glutamine

(S)-Asparagine and (S)-glutamine ortho-carboranyl derivatives with free amino and carboxy groups in the α-position were synthesized. By an example of Nγ-(1,2-dicarba-closo-dodecarboran-3-yl)-(S)-glutamine it was demonstrated that the developed synthetic approach carboranyl derivatives of amino acids allowed the preparation of optically pure isomers.

Identification of SNAIL1 Peptide-Based Irreversible Lysine-Specific Demethylase 1-Selective Inactivators

Inhibition of lysine-specific demethylase 1 (LSD1), a flavin-dependent histone demethylase, has recently emerged as a new strategy for treating cancer and other diseases. LSD1 interacts physically with SNAIL1, a member of the SNAIL/SCRATCH family of transcription factors. This study describes the discovery of SNAIL1 peptide-based inactivators of LSD1. We designed and prepared SNAIL1 peptides bearing a propargyl amine, hydrazine, or phenylcyclopropane moiety. Among them, peptide 3, bearing hydrazine, displayed the most potent LSD1-inhibitory activity in enzyme assays. Kinetic study and mass spectrometric analysis indicated that peptide 3 is a mechanism-based LSD1 inhibitor. Furthermore, peptides 37 and 38, which consist of cell-membrane-permeable oligoarginine conjugated with peptide 3, induced a dose-dependent increase of dimethylated Lys4 of histone H3 in HeLa cells, suggesting that they are likely to exhibit LSD1-inhibitory activity intracellularly. In addition, peptide 37 decreased the viability of HeLa cells. We believe this new approach for targeting LSD1 provides a basis for development of potent selective inhibitors and biological probes for LSD1.