35737-15-6

Basic information

• Product Name: Nalpha-FMOC-L-Tryptophan
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-TRYPTOPHAN;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-TRYPTOPHAN;N-(9-FLUORENYLMETHOXYCARBONYL)-L-TRYPTOPHAN;N-9-FLUORENYLMETHYLOXYCARBONYL-L-TRYPTOPHAN;N-ALPHA-FMOC-L-TRYPTOPHAN;NALPHA-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-TRYPTOPHAN;FMOC-TRP;FMOC-TRYPTOPHAN
• CAS NO: 35737-15-6
• Molecular Formula: C₂₆H₂₂N₂O₄
• Molecular Weight: 426.46
• EINECS: 252-706-5
• Product Categories: Protected Amino Acids;Amino Acid Derivatives;Amino Acids;Tryptophan [Trp, W];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Indoles;Tryptophans;Fmoc-Amino acid series
• Mol File: 35737-15-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 182-185 °C(lit.)
• Boiling Point: 541.92°C (rough estimate)
• Flash Point: 384.3 °C
• Appearance: white to off-white crystalline powder
• Density: 1.2501 (rough estimate)
• Vapor Pressure: 2.87E-21mmHg at 25°C
• Refractive Index: -28.5 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Pyridine
• PKA: 3.89±0.10(Predicted)
• BRN: 4216624
• CAS DataBase Reference: Nalpha-FMOC-L-Tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: Nalpha-FMOC-L-Tryptophan(35737-15-6)
• EPA Substance Registry System: Nalpha-FMOC-L-Tryptophan(35737-15-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26
• WGK Germany: 3
• Hazardous Substances Data: 35737-15-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Nα-Fmoc-L-tryptophan is an N-Fmoc protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.

InChI:InChI=1/C26H22N2O4/c29-25(30)24(13-16-14-27-23-12-6-5-7-17(16)23)28-26(31)32-15-22-20-10-3-1-8-18(20)19-9-2-4-11-21(19)22/h1-12,14,22,24,27H,13,15H2,(H,28,31)(H,29,30)/p-1/t24-/m0/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 6159-33-7 L-tryptophan hydrochloride 
• 1131148-55-4 1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole 
• 73-22-3 L-Tryptophan 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 20696-57-5 L-tryptophanamide 

Downstream Products

• 865619-25-6 1-(2-fluoro-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 

Relevant articles and documents

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.

Liquid-chromatography quantitative analysis of 20 amino acids after derivatization with FMOC-CI and its application to different origin Radix isatidis

We developed a simple, rapid and reliable method for determination of 20 common amino acids based on derivatization with 9-fluorenylmethyl chloroformate (FMOC-CI) and RP-LC/UV, this method was first introduced into quantitative analysis of amino acids. The amino groups of amino acids were trapped with FMOC-CI to form amino acid-FMOC-Cl adducts which can be suitable for LC-UV. Chromatographic separation was performed on a C18 column with a mobile phase gradient consisting of acetonitrile and sodium acetate solution. This method was shown to be sensitive for 20 common amino acids. In the intra-day precisions assay, the range of RSDs was 3.21-7.67% with accuracies of 92.34-102.51%; for the inter-day precisions assay, the range of RSDs was 5.82-9.19% with accuracies of 90.25-100.63%. The results also indicated that solutions of amino acids-FMOC-Cl can be kept at room temperature for at least 24 h without showing significant losses in the quantified values. The validated method was successfully applied to the determination of major four kinds of amino acids in R. isatidis samples (Arg, Pro, Met and Val). The total content of amino acids in different origin R. isatidis was 13.32-19.16 mg/g. The differences between R. isatidis samples were large using HCA.