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

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

Uses

Used in Pharmaceutical Industry:
Nalpha-FMOC-L-Tryptophan is used as an intermediate in the synthesis of various pharmaceutical compounds for its role in cell proliferation and protein biosynthesis. Its protective N-Fmoc group aids in the selective protection of the amino group during chemical reactions, ensuring the successful synthesis of target molecules.
Used in Neurotransmitter Research:
Nalpha-FMOC-L-Tryptophan is used as a research compound in the study of Serotonin, a neurotransmitter that plays a vital role in sleep, mood regulation, and cognitive functions. Understanding the biosynthesis and role of Serotonin can lead to the development of new treatments for various neurological and psychiatric disorders.
Used in Amino Acid Derivatives:
Nalpha-FMOC-L-Tryptophan is used as a building block in the synthesis of various amino acid derivatives, which can be utilized in the development of new drugs, bioactive compounds, and materials with specific properties.
Used in Eosinophilia-Myalgia Syndrome Research:
Nalpha-FMOC-L-Tryptophan is used as a research tool to study the eosinophilia-myalgia syndrome, a rare disorder associated with the ingestion of L-Tryptophan. Understanding the molecular mechanisms behind this syndrome can help in the development of preventive measures and potential treatments.

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

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

Downstream Products

• 71989-37-2 Fmoc-Trp-ONp 
• 113534-39-7 Fmoc-Trp-OTDO 
• 13139-14-5 Boc-Trp-OH 
• 86069-87-6 N-α-fluorenylmethoxycarbonyl-L-tryptophan pentafluorophenyl ester 
• 126771-48-0 (S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)-propionic acid 4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl ester 
• 115748-09-9 Fmoc-Trp-ODhbt 
• 33515-09-2 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolylglycinamide 
• 25126-32-3 cholecystokinin octapeptide 
• 263841-90-3 (2S,3S)-2-{(2S,3S)-2-[(S)-2-[(S)-2-((S)-2-Amino-3-phenyl-propionylamino)-4-carbamoyl-butyrylamino]-3-(1H-indol-3-yl)-propionylamino]-3-methyl-pentanoylamino}-3-methyl-pentanoic acid 
• 865619-24-5 1-(4-chloro-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.

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

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.

A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids

The study describes a new "one-pot" route to the synthesis of N-9-fluorenylmethyloxycarbonyl (Fmoc) α-amino diazoketones. The procedure was tested on a series of commercially available free or side-chain protected α-amino acids employed as precursors. The conversion into the title compounds was achieved by masking and activating the α-amino acids with a single reagent, namely, 9-fluorenylmethyl chloroformate (Fmoc-Cl). The resulting N-protected mixed anhydrides were reacted with diazomethane to lead to the α-amino diazoketones, which were isolated by flash column chromatography in very good to excellent overall yields. The versatility of the procedure was verified on lipophilic α-amino acids and further demonstrated by the preparation of N-Fmoc-α-amino diazoketones also from α-amino acids containing side-chain masking groups, which are orthogonal to the Fmoc one. The results confirmed that tert-butyloxycarbonyl (Boc), tert-butyl (tBu), and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf), three acid-labile protecting groups mostly adopted in the solution and solid-phase peptide synthesis, are compatible to the adopted reaction conditions. In all cases, the formation of the corresponding C-methyl ester of the starting amino acid was not observed. Moreover, the proposed method respects the chirality of the starting α-amino acids. No racemization occurred when the procedure was applied to the synthesis of the respective N-Fmoc-protected α-amino diazoketones from l-isoleucine and l-threonine and to the preparation of a diastereomeric pair of N-Fmoc-protected dipeptidyl diazoketones.

Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids

Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20° as reagents to introduce -amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC. Georg Thieme Verlag Stuttgart - New York.

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.

New regioselective derivatives of sucrose with amino acid and acrylic groups

We report here a range of new sucrose derivatives obtained from '3-ketosucrose' in aqueous medium with few reaction steps. As an intermediate, 3-amino-3-deoxy-α-d-allopyranosyl β-d-fructofuranoside (1) was obtained via the classical route of reductive amination with much improved yield and high stereoselectivity. Building blocks for polymerization were synthesized by introduction of acrylic-type side chains, for example, with methacrylic anhydride. Corresponding polymers were synthesized. Aminoacyl and peptide conjugates were obtained through conventional peptide synthesis with activated and protected amino acids. Deprotection yielded new glycoderivatives having an unconventional substitution pattern, namely 3-(aminoacylamino) allosaccharides. Both mono- and di-peptide conjugates of allosucrose have been synthesized.

A novel and efficient method for cleavage of phenacylesters by magnesium reduction with acetic acid

(Equation Presented) In the present study, we use magnesium turnings as a new deprotection reagent for the phenacyl group during orthogonal organic synthesis in the presence of other esters and sensitive protecting groups. By applying the new magnesium turnings/acetic acid deprotection method, phenacyl group can be more easily combined with other protecting groups that are not compatible with the zinc/acetic acid method.

An Effective Water-Free Aprotic System for Dissolving Free Amino Acids

An effective water-free system was proposed for dissolution and subsequent use in peptide synthesis of free amino acids and their derivatives. It consists of dimethylformamide, a tertiary base, and inorganic additives. Neutral salts (CF3COONa, Ba(ClO4)2, Ca(ClO4)2, NaClO4, BaI2, or Ca(NO3)2) serve as the inorganic additives that increase the solubility of free amino acids in dimethylformamide and provide true 0.2-3 M amino acid solutions. Triethylamine and N-methylmorpholine are most suitable as the tertiary bases. This system was used in reactions with acylating agents: Boc2O, ZOSu, FmocOSu, and activated derivatives of Nα-protected amino acids or peptides. The corresponding amino acid derivatives or Nα-protected di-, tri-, and tetrapeptides were obtained in yields of 80-99 percent at the reaction times of 30-240 min.

Apparatus and methods for detecting antibodies

A single, unitary, solid phase support apparatus having a planar surface divided into a plurality of separate zone functions to detect antibodies. Each zone has bonded to it, a different peptide through its C-terminal end. The zones are incubated with the analyte sample and observed for reaction, indicating the virus-specific or bacteria specific presence or absence.