200623-62-7

Basic information

• Product Name: N-Fmoc-N'-trityl-D-glutamine
• Synonyms: FMOC-D-GLN(TRT)-OH;FMOC-D-GLN(TRT);FMOC-D-GLUTAMINE(TRITYL);FMOC-D-GLUTAMINE(TRT)-OH;FMOC-N-DELTA-TRITYL-D-GLUTAMINE;N-ALPHA-FMOC-N-GAMMA-TRITYL-D-GLUTAMINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-GAMMA-TRITYL-D-GLUTAMINE;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-N-OMEGA-TRITYL-D-GLUTAMINE
• CAS NO: 200623-62-7
• Molecular Formula: C39H34N2O5
• Molecular Weight: 610.7
• Product Categories: Amino Acids;Glutamine [Gln, Q];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 200623-62-7.mol

Chemical Properties

• Melting Point: 232-237°C
• Boiling Point: 873.5 °C at 760 mmHg
• Flash Point: 482.1 °C
• Appearance: /
• Density: 1.256
• Storage Temp.: -20°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMF (Sparingly)
• PKA: 3.73±0.10(Predicted)
• CAS DataBase Reference: N-Fmoc-N'-trityl-D-glutamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-N'-trityl-D-glutamine(200623-62-7)
• EPA Substance Registry System: N-Fmoc-N'-trityl-D-glutamine(200623-62-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 200623-62-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
N-Fmoc-N'-trityl-D-glutamine is used as a building block for the synthesis of various complex molecules, including pharmaceuticals and bioactive compounds. Its application in this field is attributed to its compatibility with a wide range of chemical reactions and its ability to be easily incorporated into larger molecular structures.
Used in Peptide Chemistry:
In peptide chemistry, N-Fmoc-N'-trityl-D-glutamine serves as a crucial component in the construction of peptide sequences. It is used as a protected amino acid, which aids in the stepwise assembly of peptides while preventing unwanted side reactions. The trityl group provides a stable protection for the amino group, ensuring the selective deprotection and coupling of subsequent amino acids during peptide synthesis.
Used in Pharmaceutical Industry:
N-Fmoc-N'-trityl-D-glutamine is used as a key intermediate in the development of novel drugs and therapeutic agents. Its application in this industry is due to its ability to be modified and incorporated into various drug candidates, potentially leading to the discovery of new treatments for a range of diseases and conditions.
Used in Research and Development:
In the field of research and development, N-Fmoc-N'-trityl-D-glutamine is utilized as a valuable tool for studying the properties and functions of amino acids and peptides. Its use in this context allows scientists to gain a deeper understanding of the molecular mechanisms underlying various biological processes and to develop new strategies for targeting specific biological pathways.

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 71989-20-3 N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 102747-84-2 5-trityl-L-glutamine 
• 132388-60-4 (S)-2-(((benzyloxy)carbonyl)amino)-5-oxo-5-(tritylamino)pentanoic acid 
• 2650-64-8 Cbz-L-Gln 
• 56-85-9 L-glutamine 

Downstream Products

• 125882-62-4 fellutamide B 
• 326494-25-1 C₇₇H₁₂₉N₂₁O₂₂ 

Relevant articles and documents

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Total of 22 caged xanthones were subjected to susceptibility testing of global epidemic MRSA USA300. Natural morellic acid showed the strongest potency (MIC of 12.5 μM). However, its potent toxicity diminishes MRSA therapeutic potential. We synthetically modified natural morellic acid to yield 13 derivatives (3a-3m). Synthetically modified 3b retained strong potency in MRSA growth inhibition, yet the toxicity was 20-fold less than natural morellic acid, permitting the possibility of using caged xanthones for MRSA therapeutic.

Mild oxidative cleavage of 9-BBN-protected amino acid derivatives

Protection of the amino acid moiety using 9-BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9-BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90% yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine. A representative set of 9-BBN-protected amino acid derivatives were efficiently deprotected using peracid reagents in excellent yields. Deprotection is orthogonal with several common protecting groups. Its tolerance of highly acid sensitive groups, such as trityl-protected amides and glycosidic linkages, is especially notable.

NOVEL PEPTIDES DERIVED FROM NCAM (FGLs)

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DIPHENYLMETHANE COMPOUND

Compounds having a diphenylmethane skeleton are superior in broad utility and stability, and are useful as a protecting reagent (anchor) of amino acid and/or peptide in the liquid phase synthesis and the like of a peptide having a C-terminal etc., which are of a carboxamide(-CONHR)-type, and in organic synthetic reaction methods (particularly peptide liquid phase synthetic methods), and may be contained in a kit for peptide liquid phase synthesis.

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Protected amino acids and process for the preparation thereof

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Protection of carboxamide functions by the trityl residue. Application to peptide synthesis

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