Nalpha-FMOC-L-Tryptophan

Base Information

• Chemical Name: Nalpha-FMOC-L-Tryptophan
• CAS No.: 35737-15-6
• Molecular Formula: C26H22N2O4
• Molecular Weight: 426.472
• Hs Code.: 2933 99 80
• European Community (EC) Number: 252-706-5
• Nikkaji Number: J256.557I
• Wikidata: Q69757079
• ChEMBL ID: CHEMBL292051
• Mol file: 35737-15-6.mol

Synonyms:Fmoc-Trp-OH;35737-15-6;Fmoc-L-tryptophan;Nalpha-FMOC-L-Tryptophan;Fmoc-L-Trp-OH;L-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;CHEMBL292051;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-TRYPTOPHAN;MFCD00037126;(s)-2-(((9h-fluoren-9-yl)methoxy)carbonylamino)-3-(1h-indol-3-yl)propanoic acid;(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)-propionic acid;N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-tryptophan;EINECS 252-706-5;N--Fmoc-L-tryptophan;N-|A-Fmoc-L-tryptophan;9-FLUORENYLMETHOXYCARBONYL-L-TRYPTOPHAN;MLS001359854;SCHEMBL119372;Fmoc-L-Trp-OH Fmoc-L-tryptophan;HMS3030J08;BDBM50043810;AKOS012535969;AKOS015924240;AC-8601;AM82281;CS-W011637;(S)-2-((((9H-FLUOREN-9-YL)METHOXY)CARBONYL)AMINO)-3-(1H-INDOL-3-YL)PROPANOIC ACID;Fmoc-Trp-OH, >=97.0% (HPLC);NCGC00247299-01;AS-12714;SMR001224401;F0307;EN300-81250;M03374;A822965;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]tryptophan #;N-9-FLUORENYLMETHYLOXYCARBONYL-L-TRYPTOPHAN;(((9H-Fluoren-9-yl)methoxy)carbonyl)-L-tryptophan;J-300269;Q-101610;Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-tryptophan;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-tryptophan (Fmoc-L-Trp-OH);(2R)-2-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}-3-(1H-INDOL-3-YL)PROPANOIC ACID;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(1H-indol-3-yl)propanoic acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)propanoate

Chemical Property of Nalpha-FMOC-L-Tryptophan

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 2.87E-21mmHg at 25°C
• Melting Point: 183-185 °C
• Refractive Index: -28.5 ° (C=1, DMF)
• Boiling Point: 711.9 °C at 760 mmHg
• PKA: 3.89±0.10(Predicted)
• Flash Point: 384.3 °C
• PSA: 91.42000
• Density: 1.35 g/cm³
• LogP: 5.09320
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in Pyridine
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 426.15795719
• Heavy Atom Count: 32
• Complexity: 663

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-Trp ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)O
• 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.

Technology Process of Nalpha-FMOC-L-Tryptophan

There total 13 articles about Nalpha-FMOC-L-Tryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Fmoc-Trp-OH (35737-15-6)

Guidance literature:

With sodium perchlorate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield: 91.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Fmoc-Trp-OH (35737-15-6)

Guidance literature:

With sodium carbonate; In acetone; at 0 - 20 ℃;

DOI:10.1016/j.carres.2005.11.033

Reference yield: 89.0%

(9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Fmoc-Trp-OH (35737-15-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

upstream raw materials:

(9-fluorenyl)methyl pentafluorophenyl carbonate

L-Tryptophan

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

Fmoc-Trp-ONp

(R)-3-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-N-{(S)-1-[(R)-1-((S)-1-hydrazinocarbonyl-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-3-methyl-butyl}-succinamic acid tert-butyl ester

cholecystokinin octapeptide

(R)-3-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-4-{(S)-2-[(R)-1-((S)-1-hydrazinocarbonyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-4-oxo-butyric acid tert-butyl ester

Refernces

• 1、 Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong. "Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety". . p. 1080 - 1090. Retrieved 2020/05/25.
• 2、 Siciliano, Carlo,De Marco, Rosaria,Guidi, Ludovica Evelin,Spinella, Mariagiovanna,Liguori, Angelo. "A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids". . p. 10575 - 10582. Retrieved 2013/02/22.