Fmoc-L-Isoleucine

Base Information

• Chemical Name: Fmoc-L-Isoleucine
• CAS No.: 71989-23-6
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• Hs Code.: 2924 29 70
• NSC Number: 334289
• DSSTox Substance ID: DTXSID70868058
• Mol file: 71989-23-6.mol

Synonyms:(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-pentanoate;N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-isoleucine;(2S,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-pentanoate;Fmoc-L-Ile-OH;Fmoc-lle-OH;N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine;N-(9-Fluorenylmethoxycarbonyl)-L-isoleucine;

Chemical Property of Fmoc-L-Isoleucine

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 2.28E-13mmHg at 25°C
• Melting Point: 145-147 °C(lit.)
• Refractive Index: -12 ° (C=1, DMF)
• Boiling Point: 559.8 °C at 760 mmHg
• PKA: 3.92±0.22(Predicted)
• Flash Point: 292.4 °C
• PSA: 75.63000
• Density: 1.207 g/cm³
• LogP: 4.41530
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol (very faint turbidity).
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 486

Purity/Quality:

99%, ^*data from raw suppliers

Fmoc-L-isoleucine 99+% ^*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

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: N-Fmoc-L-isoleucine is an unnatural amino acid used for peptidomimetics. It is also used as a pharmaceutical intermediate.

Technology Process of Fmoc-L-Isoleucine

There total 12 articles about Fmoc-L-Isoleucine 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: 89.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Ile-OH (71989-23-6,251316-98-0)

Guidance literature:

With calcium(II) nitrate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield: 88.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester → Fmoc-Ile-OH (71989-23-6,251316-98-0)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2017.03.021

Reference yield: 84.0%

N-Fmoc-L-isoleucine methyl ester → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine (71989-23-6,251316-98-0)

Guidance literature:

With aluminium trichloride; N,N-dimethyl-aniline; In dichloromethane;

DOI:10.1002/ejoc.200400321

upstream raw materials:

L-isoleucine

9-fluorenylmethyl N-succinimidyl carbonate

(9-fluorenyl)methyl pentafluorophenyl carbonate

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

Downstream raw materials:

N-α-Fmoc-L-isoleucine pentafluorophenyl ester

N-Fmoc-Ile-Phe-Ser(Bu^t)-Pro-Ile-Pro-OBu^t

(Sar1)angiotensin II

N-Fmoc-Ile-Phe-Pro-O-Bu-t

Refernces

• 1、 Goldschmidt G?z, Viktória,Nagy, Adrienn,Farkas, Viktor,Keszei, Ern?,Perczel, András. "Unwanted hydrolysis or α/β-peptide bond formation: How long should the rate-limiting coupling step take?". . p. 30720 - 30728. Retrieved 2019/10/28.
• 2、 Chaiyakunvat, Pongkorn,Anantachoke, Natthinee,Reutrakul, Vichai,Jiarpinitnun, Chutima. "Caged xanthones: Potent inhibitors of global predominant MRSA USA300". supporting information. p. 2980 - 2983. Retrieved 2016/06/13.