13726-85-7

Basic information

• Product Name: N-(tert-Butoxycarbonyl)-L-glutamine
• Synonyms: n2-[(1,1-dimethylethoxy)carbonyl]-l-glutamin;BOC-GLN;BOC-GLUTAMINE;BOC-L-GLUTAMINE;BOC-L-GLN;BOC-L-GLN-OH;TBOC-L-GLUTAMINE;T-BUTYLOXYCARBONYL-L-GLUTAMINE
• CAS NO: 13726-85-7
• Molecular Formula: C₁₀H₁₈N₂O₅
• Molecular Weight: 246.26
• EINECS: 237-296-8
• Product Categories: Amino Acid Derivatives;Amino Acids;Glutamine [Gln, Q];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series;Amino Acids & Derivatives;Chiral Reagents
• Mol File: 13726-85-7.mol
• Article Data: 26

Chemical Properties

• Melting Point: 113-116 °C (dec.)(lit.)
• Boiling Point: 389.26°C (rough estimate)
• Flash Point: 261.7 °C
• Appearance: White fine crystalline powder
• Density: 1.2430 (rough estimate)
• Vapor Pressure: 9.65E-12mmHg at 25°C
• Refractive Index: -4 ° (C=2, EtOH)
• Storage Temp.: −20°C
• Solubility: Soluble in DMSO and methanol. Soluble in 1 mmole in 2 ml DMF.
• PKA: 3.84±0.10(Predicted)
• BRN: 2127805
• CAS DataBase Reference: N-(tert-Butoxycarbonyl)-L-glutamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)-L-glutamine(13726-85-7)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)-L-glutamine(13726-85-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 13726-85-7(Hazardous Substances Data)

Usage

Chemical Properties

White fine crystalline powder

Uses

Different sources of media describe the Uses of 13726-85-7 differently. You can refer to the following data:
1. Protected Glutamine.
2. It is employed in the synthesis and analgesic activity of human .beta.-endorphin.

InChI:InChI=1/C10H18N2O5/c1-10(2,3)17-9(16)12-6(8(14)15)4-5-7(11)13/h6H,4-5H2,1-3H3,(H2,11,13)(H,12,16)(H,14,15)/p-1/t6-/m0/s1

Upstream product

• 56-85-9 L-glutamine 
• 18595-34-1 tert-butyl fluoroformate 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 45214-91-3 (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid 
• 56-86-0 L-glutamic acid 
• 227006-17-9 4-guanidinophenyl N^α-tert-butoxycarbonyl-L-glutaminate 
• 98115-14-1 N^α,N^ca-di-tert-butyloxycarbonylglutamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 25691-37-6 (2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid 
• 16748-29-1 N^α-Methyl-L-ornithin 
• 61543-21-3 (S)-benzyl 5-amino-2-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 133565-42-1 tert-butyl N-[(2S)-4-carbamoyl-1-hydroxybutan-2-yl]carbamate 
• 1053694-32-8 ((S)-3-Carbamoyl-1-{(S)-2-carbamoyl-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-ethylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 1055030-15-3 [(S)-3-Carbamoyl-1-({(S)-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-phenyl-methyl}-carbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 1054662-75-7 ((S)-3-Carbamoyl-1-{(S)-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-3-methyl-butylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 1053734-69-2 ((S)-3-Carbamoyl-1-{(S)-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-2,2-dimethyl-propylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 1055032-66-0 ((S)-3-Carbamoyl-1-{(1S,2S)-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-2-methyl-butylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 1053613-00-5 ((S)-3-Carbamoyl-1-{(S)-1-[(S)-2-cyclohexyl-1-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 151782-02-4 Boc-Gln-Val-OPac 
• 126088-82-2 Boc-Gln-D-Trp(CHO)-Phe-OBzl 

Relevant articles and documents

Structural design and synthesis of bimodal PNA that simultaneously binds two complementary DNAs to Form fused double duplexes

Bimodal PNAs are new PNA constructs designed to bind two different cDNA sequences synchronously to form double duplexes. They are synthesized on solid phase using sequential coupling and click reaction to introduce a second base in each monomer at Cα via alkyltriazole linker. The ternary bimodal PNA:DNA complexes show stability higher than that of individual duplexes. Bimodal PNAs are appropriate to create higher-order fused nucleic acid assemblies.

A PROCESS FOR THE PREPARATION OF L-GLUTAMINE

The present invention relates to a process for the preparation of L-Glutamine of Formula (I). The present invention also relates to an improved process for the purification of L-Glutamine of Formula (I) having specific bulk density and Hausner ratio.

Preparation method of 3-amino-2,6-piperidinedione hydrochloride

The invention discloses a preparation method of 3-amino-2,6-piperidinedione hydrochloride. The method comprises the following steps that (1) L-glutamine is protected in an alkaline medium to obtain N-tert-butyl oxyformyl-L-glutamine; (2) under the anhydrous condition, the N-tert-butyl oxyformyl-L-glutamine obtained in step (1) and N,N-carbonyldiimidazole are subjected to cyclization under catalysis of 4-dimethylamino pyridine to obtain N-tert-butyl oxyformyl-3-amino-2,6-piperidinedione; (3) the N-tert-butyl oxyformyl-3-amino-2,6-piperidinedione obtained in step (2) is subjected to deprotectionin an acid medium, hydrochloride is formed, and the 3-amino-2,6-piperidinedione hydrochloride is obtained. The target product, namely the 3-amino-2,6-piperidinedione hydrochloride, is obtained by three steps including protection, cyclization, deprotection and hydrochloride forming, and the obtained product is high in purity and stable in quality. According to the preparation method, only three steps are needed in the synthesis process, the path is simple, the reaction conditions are mild, a high-pressure hydrogenation condition is not needed, the cost is low, and industrialization is easy toachieve.