2419-94-5

Basic information

• Product Name: Boc-L-Glutamic acid
• Synonyms: N-(TERT-BUTOXYCARBONYL)-L-GLUTAMIC ACID;N-T-BUTOXYCARBONYL-L-GLUTAMIC ACID;N-ALPHA-T-BOC-L-GLUTAMIC ACID;N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-GLUTAMIC ACID;BOC-GLU-OH;BOC-GLUTAMIC ACID-OH;BOC-L-GLU-OH
• CAS NO: 2419-94-5
• Molecular Formula: C₁₀H₁₇NO₆
• Molecular Weight: 247.25
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 2419-94-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: ~110 °C (dec.)
• Boiling Point: 390.28°C (rough estimate)
• Flash Point: 217.4 °C
• Appearance: white to off-white crystalline powder
• Density: 1.2868 (rough estimate)
• Vapor Pressure: 8.13E-09mmHg at 25°C
• Refractive Index: -15 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• PKA: 3.83±0.10(Predicted)
• Water Solubility: Soluble in water
• BRN: 2418563
• CAS DataBase Reference: Boc-L-Glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-Glutamic acid(2419-94-5)
• EPA Substance Registry System: Boc-L-Glutamic acid(2419-94-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26-4/25
• WGK Germany: 3
• Hazardous Substances Data: 2419-94-5(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Uses

N-Boc-L-glutamic acid is an N-Boc-protected form of L-Glutamic acid (G596960). L-Glutamic acid is a nonessential amino acid that is important to the mammalian central nervous system. L-Glutamic acid is also a neurotransmitter for cone photoreceptors in the human brain and is used as a treatment for patients who have liver disease accompanied by encephalopathy (a condition termed ‘hepatic coma’).

InChI:InChI=1/C10H17NO6/c1-10(2,3)17-9(16)11-6(8(14)15)4-5-7(12)13/h6H,4-5H2,1-3H3,(H,11,16)(H,12,13)(H,14,15)/t6-/m1/s1

Upstream product

• 98115-14-1 N^α,N^ca-di-tert-butyloxycarbonylglutamine 
• 24277-38-1 (S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate 

Downstream Products

• 82198-69-4 BocLys(2ClZ)-Arg(Tos)-Lys(2ClZ)-Arg(Tos)-Gln-GlnNH₂ 
• 144800-42-0 Boc-Glu-OAbc 
• 200399-54-8 (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-[(benzhydryl-carbamoyl)-methyl] ester 
• 406500-98-9 Phe-Glu-βAla 
• 1041478-28-7 Boc-Glu(OPfp)-OPfp 
• 227006-23-7 Boc-L-Glu-OGp 
• 56-86-0 L-glutamic acid 
• 149-87-1 Pyroglutamic acid 
• 300409-91-0 C₂₆H₃₅N₃O₈ 
• 1246611-79-9 C₄₅H₆₃N₉O₁₂ 
• 103032-40-2 N-(4-nitro-benzoyl)-L-glutamic acid bis-benzylamide 

Relevant articles and documents

Enzymatic removal of carboxyl protecting groups. 2. Cleavage of the benzyl and methyl moieties

Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.

PROPERTIES OF Nα,Nca-DI-TERT-BUTYLOXYCARBONYL-ω-CARBAMOYL-α-AMINO ACIDS AND DIRECT SYNTHESIS OF PROTECTED HOMOGLUTAMIC ACID DERIVATIVES

The protected carboxamide function of Nα,Nca-di-tert-butyloxy-carbonyl-ω-carbamoyl-α-amino acids worked well with nucleophilic reagents.Applying this novel reactivity, we developed an efficient synthetic route to Nα-tert-butyloxycarbonylhomoglutamic acid and its derivatives, including Nα-tert-butyloxycarbonylhomoglutamic acid δ-benzyl ester, from Nα,Nca-di-tert-butyloxycarbonylhomoglutamine.KEYWORDS - protected homoglutamic acid synthesis; Nca-tert-butyloxycarbonylated carboxamide; hydrolysis; selective deprotection; Nα-tert-butyloxycarbonylhomoglutamic acid δ-benzyl ester; Nα-tert-butyloxycarbonylhomoglutamic acid α-tert-butyl ester; Nα-tert-butyloxycarbonylhomoglutamine; optical purity