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

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

Uses

1. Used in Pharmaceutical Industry:
N-(tert-Butoxycarbonyl)-L-glutamine is used as a protected amino acid for the synthesis of various pharmaceutical compounds, including human .beta.-endorphin, which is a potent analgesic agent. The Boc-protecting group allows for the selective protection of the amino group during the synthesis process, ensuring the desired product is obtained without unwanted side reactions.
2. Used in Peptide Synthesis:
N-(tert-Butoxycarbonyl)-L-glutamine is used as a protected amino acid building block for the synthesis of peptides. The Boc-protecting group is particularly useful in solid-phase peptide synthesis (SPPS), where it helps to prevent side reactions and improve the overall yield of the desired peptide product.
3. Used in Research and Development:
N-(tert-Butoxycarbonyl)-L-glutamine is also used in research and development for the study of peptide chemistry, protein structure, and function. The Boc-protected form of L-glutamine allows researchers to explore the effects of amino acid modifications on peptide and protein properties, as well as to develop new synthetic strategies for peptide synthesis.

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

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 56-85-9 L-glutamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 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 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 18595-34-1 tert-butyl fluoroformate 

Downstream Products

• 63094-77-9 Boc-Gln-ONb 
• 101924-88-3 tert-butyloxycarbonylglutamine phenylhydrazide 
• 61543-21-3 (S)-benzyl 5-amino-2-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 875434-02-9 10-(N-α-tert-butoxycarbonyl-L-glutaminyl)aminogoniothalamin 
• 870196-24-0 {1-[2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester 
• 77345-20-1 (S)-N-α-tert-butoxycarbonylglutamineamide 
• 416853-05-9 {2,6-bis-[3-(2-tert-butoxycarbonylamino-4-carbamoyl-butyrylamino)-propionylamino]-pyridin-4-yloxy}-acetic acid benzyl ester 
• 163887-48-7 Tyr-Ile-Asn-Leu-Ile-Thr-Arg-Gln-Arg-Tyr-NH2 
• 145274-93-7 dYdL(NMe)FQPQRFamide 
• 145274-93-7 D-Tyr-Leu-(N-methyl)Phe-Gln-Pro-Gln-Arg-Phe-NH2 
• 124256-00-4 dYdLdFQPQRFamide 
• 124256-00-4 D-Tyr-D-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2 
• 124256-00-4 Tyr-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2 

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.

Peptide Nucleic Acid with Double Face: Homothymine-Homocytosine Bimodal Cα-PNA (bm-Cα-PNA) Forms a Double Duplex of the bm-PNA2:DNA Triplex

Cα-bimodal peptide nucleic acids (bm-Cα-PNA) are PNAs with two faces and are designed homologues of PNAs in which each aminoethylglycine (aeg) repeating unit in the standard PNA backbone hosts a second nucleobase at Cα through a spacer chain with a triazole linker. Such bm-Cα-PNA with mixed sequences can form double duplexes by simultaneous binding to two complementary DNAs, one to the base sequence on t-amide side and the other to the bases on the Cα side chain. The synthesis of bm-Cα-PNA with homothymine (T7) on the t-amide face and homocytosine (C5) on the Cα side chain through the triazole linker was achieved by solid phase synthesis with the global click reaction. In the presence of complementary DNAs dA8 and dG6 at neutral pH, bm-Cα-PNA 1 forms a higher order pentameric double duplex of a triplex composed of two bm-Cα-PNA-C5:dG5 duplexes built on a core (bm-Cα-PNA-T7)2:dA8 triplex. Circular dichroism studies showed that assembly can be achieved by either triplex first and duplex later or vice versa. Isothermal titration calorimetry data indicated that the assembly is driven by favorable enthalpy. These results validate concurrent multiple complex formation by bimodal PNAs with additional nucleobases at Cα or Cγon the aeg-PNA backbone and open up ways to design programmed supramolecular 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.

Cγ(S/ R)-Bimodal Peptide Nucleic Acids (Cγ- bm-PNA) Form Coupled Double Duplexes by Synchronous Binding to Two Complementary DNA Strands

Peptide nucleic acids (PNAs) are linear equivalents of DNA with a neutral acyclic polyamide backbone that has nucleobases attached via tert-amide link on repeating units of aminoethylglycine. They bind complementary DNA or RNA with sequence specificity to form hybrids that are more stable than the corresponding DNA/RNA self-duplexes. A new type of PNA termed bimodal PNA [Cγ(S/R)-bm-PNA] is designed to have a second nucleobase attached via amide spacer to a side chain at Cγon the repeating aeg units of PNA oligomer. Cγ-bimodal PNA oligomers that have two nucleobases per aeg unit are demonstrated to concurrently bind two different complementary DNAs, to form duplexes from both tert-amide side and Cγside. In such PNA:DNA ternary complexes, the two duplexes share a common PNA backbone. The ternary DNA 1:Cγ(S/R)-bm-PNA:DNA 2 complexes exhibit better thermal stability than the isolated duplexes, and the Cγ(S)-bm-PNA duplexes are more stable than Cγ(R)-bm-PNA duplexes. Bimodal PNAs are first examples of PNA analogues that can form DNA2:PNA:DNA1 double duplexes via recognition through natural bases. The conjoined duplexes of Cγ-bimodal PNAs can be used to generate novel higher-level assemblies.

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.

Preparation method of L-2,4-diaminobutyrate hydrochloride

The invention belongs to the technical field of organic chemistry, and discloses a preparation method of L-2,4-diaminobutyrate hydrochloride. The method includes the following steps that S1, L-glutamine is subjected to Boc protection under an alkaline condition to obtain a N-BOC-L-glutamine aqueous solution; S2, a saturated sodium hypochlorite solution is dropwise added into the N-Boc-L-glutamineaqueous solution obtained in the S1 for a degradation reaction, and a L-2-N-Boc-4-aminobutyric acid crude product solution is obtained; S3, the L-2-N-Boc-4-aminobutyric acid crude product solution iscondensed, the pH is adjusted with 2N hydrochloric acid, salt is removed with cation exchange resin, dilute ammonia water is used as an elution agent for elution, the eluent is condensed, concentratedhydrochloric acid is added for adjusting the pH of a concentrated solution, absolute ethyl alcohol is added, and after crystallization, filtering and drying, the L-2,4-diaminobutyrate hydrochloride is obtained. The method has the advantages that the synthetic route is short, operation is simple, three wastes pollution is less, the yield is high and the cost is low, and the method is an ideal scheme for industrial scale-up production.

(S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method

The present invention relates to a (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method. According to the method, L-glutamine is used as a raw material, the alpha-amino of the L-glutamine is protected with a protection group, a decarbonylating agent is added, a Hofmann degradation reaction is performed to remove the carbonyl group attached to the remaining amino, the protection group is removed to obtain L-2,4-diaminobutyric acid, and finally the prepared L-2,4-diaminobutyric acid and trimethyl orthoacetate are subjected to a ring forming reaction to obtain the (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid. Compared to the method in the prior art, the method of the present invention has the following characteristics that the chemical synthesis route is provided, the steps of the synthesis process are simple, the raw materials are easy to obtain, the product purity is high, and the method is suitable for large-scale industrial production.

CATIONIC LIPID CORDIARIMIDE HYBRID COMPOUNDS AND A PROCESS FOR PREPARATION THEREOF

The present invention relates to the cationic lipid cordiaroimide hybrid compounds of formula I. The present invention provides a process for preparation of these compounds is also being elaborated. The compounds described provides anticancerous activity against cell lines including PC-3 (prostate cancer), HepG2 (liver cancer), MCF-7 (breast cancer) and NIH/3T3 (non cancer) cells. The compound was also capable of inducing caspase-3 mediated apoptosis in HepG2 cells by arresting the cell cycle in the G1 phase. Furthermore, the compound exhibited DNA ligase I inhibition. The present class of cationic lipid cordiarimide hybrids is likely to find specific use in developing novel targeted therapies for liver and prostate cancers.

Design, synthesis and primary activity of thiomorpholine derivatives as DPP-IV inhibitors

Thirteen thiomorpholine-bearing compounds were designed and synthesized as dipeptidyl peptidase IV (DPP-IV) inhibitors, with natural and non-natural l-amino acids as the starting materials. Their structures were characterized by 1H NMR, 13C NMR and HR-MS. The target compounds were screened for the DPP-IV inhibition, and the preliminary SAR result was obtained. Particularly, compounds 4c, 4d and 4f with good DPP-IV inhibition in vitro were further evaluated through a mouse oral glucose tolerance test (OGTT). The preliminary result showed the potential value for further studies on those thiomorpholine-bearing compounds as DPP-IV inhibitors.