Fmoc-L-Valine

Base Information

• Chemical Name: Fmoc-L-Valine
• CAS No.: 68858-20-8
• Molecular Formula: C20H21NO4
• Molecular Weight: 339.391
• Hs Code.: 29242990
• European Community (EC) Number: 272-515-0
• DSSTox Substance ID: DTXSID901317560
• Nikkaji Number: J256.553F
• Wikidata: Q106902950
• ChEMBL ID: CHEMBL560019
• Mol file: 68858-20-8.mol

Synonyms:Fmoc-Val-OH;N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-valine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butanoate;Fmoc-L-Val-OH;

Chemical Property of Fmoc-L-Valine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 5.19E-13mmHg at 25°C
• Melting Point: 143-145 °C(lit.)
• Refractive Index: -17.5 ° (C=1, DMF)
• Boiling Point: 551.8 °C at 760 mmHg
• PKA: 3.90±0.10(Predicted)
• Flash Point: 287.5 °C
• PSA: 79.12000
• Density: 1.229 g/cm³
• LogP: 3.83870
• Storage Temp.: 2-8°C
• Solubility.: Solubility in methanol gives very faint turbidity.
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 470

Purity/Quality:

≥99%, ^*data from raw suppliers

Fmoc-valine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: It is potentially useful for proteomics studies and solid phase peptide synthesis techniques. Fmoc-valine (in addition to the other amino acids) is commonly used to synthesize 4-thiazolidinones (e.g. (E)-5-(4-Ethylbenzylidene)-2-thioxothiazolidin-4-one [E925745]) and 4-metathiazanones as well.

Technology Process of Fmoc-L-Valine

There total 27 articles about Fmoc-L-Valine 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: 96.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → Fmoc-Val-OH (68858-20-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 0 - 20 ℃;

Reference yield: 91.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + 3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione (100803-86-9) → Fmoc-Val-OH (68858-20-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 12h; Ambient temperature;

DOI:10.1055/s-1985-31329

Reference yield: 90.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + (9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → Fmoc-Val-OH (68858-20-8)

Guidance literature:

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

upstream raw materials:

L-valine

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

9-fluorenylmethyl N-succinimidyl carbonate

3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione

Downstream raw materials:

Fmoc-Val-OPfp

Ac-VEID-CHO

N-α-(9-fluorenylmethyloxycarbonyl)-L-valinal

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

Refernces

• 1、 Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.. "Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones". supporting information. p. 8297 - 8302. Retrieved 2021/03/01.
• 2、 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.