Fmoc-L-aspartic acid

Base Information

• Chemical Name: Fmoc-L-aspartic acid
• CAS No.: 119062-05-4
• Molecular Formula: C₁₉H₁₇NO₆
• Molecular Weight: 355.347
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID80427054
• Nikkaji Number: J1.808.397C
• Wikidata: Q72478000
• Mol file: 119062-05-4.mol

Synonyms:119062-05-4;Fmoc-L-aspartic acid;Fmoc-Asp-OH;N-Fmoc-L-aspartic Acid;Fmoc-L-Asp-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartic Acid;FMOC-ASPARTIC ACID;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioic acid;(((9H-Fluoren-9-yl)methoxy)carbonyl)-L-aspartic acid;Aspartic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-(9-Fluorenylmethoxycarbonyl)-L-aspartic-15N acid;fmoc-aspartate;FmocAsp;Fmoc-Asp;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)succinic acid;SCHEMBL378041;DTXSID80427054;KSDTXRUIZMTBNV-INIZCTEOSA-N;MFCD00237654;AKOS015910142;AM81590;CS-W013898;HY-W013182;AC-17109;AS-47083;PD196883;F0452;EN300-81347;F11939;J-300072;Q-101796;N-(9H-Fluorene-9-ylmethoxycarbonyl)-L-aspartic acid;(S)-2-(9H-fluoren-9-ylmethoxycarbonyl-amino)succinic acid;L-ASPARTIC ACID, N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanedioic acid

Chemical Property of Fmoc-L-aspartic acid

Chemical Property:

• Vapor Pressure: 1.24E-14mmHg at 25°C
• Melting Point: 180-190 °C
• Refractive Index: 1.628
• Boiling Point: 587.2 °C at 760 mmHg
• PKA: 3.66±0.23(Predicted)
• Flash Point: 308.9 °C
• PSA: 112.93000
• Density: 1.399 g/cm³
• LogP: 2.84390
• Storage Temp.: −20°C
• Water Solubility.: Soluble in methanol, and water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 355.10558726
• Heavy Atom Count: 26
• Complexity: 528

Purity/Quality:

99% ^*data from raw suppliers

Fmoc L-aspartic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC(=O)O)C(=O)O
• Uses: N-Fmoc-L-aspartic acid is used to biosynthesize other amino acids with in the human body.

Technology Process of Fmoc-L-aspartic acid

There total 17 articles about Fmoc-L-aspartic acid 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: 98.0%

Fmoc-(tBu)Asp-OH (71989-14-5) → N-α-9-fluorenylmethoxycarbonyl-aspartic acid (136083-57-3,136083-73-3,119062-05-4)

Guidance literature:

Fmoc-(tBu)Asp-OH; With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube;

With trifluoroacetic acid; In water; acetonitrile; chemoselective reaction;

DOI:10.1002/chem.201501799

Reference yield: 96.0%

Fmoc-Asp-O-t-Bu (129460-09-9,134098-70-7) → N-α-9-fluorenylmethoxycarbonyl-aspartic acid (136083-57-3,136083-73-3,119062-05-4)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; for 0.416667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79116-7

Reference yield: 96.0%

Fmoc-Asp(otBu)-Wang resin → N-α-9-fluorenylmethoxycarbonyl-aspartic acid (136083-57-3,136083-73-3,119062-05-4)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 1h; Fmoc-Asp(OtBu)-2-CT resin chemoselective reaction; Inert atmosphere; Sealed tube; Microwave irradiation;

DOI:10.1002/chem.201501799

upstream raw materials:

L-Aspartic acid

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

Fmoc-Asp-O-t-Bu

9-fluorenylmethyl N-succinimidyl carbonate

Downstream raw materials:

C₈₆H₁₂₆N₁₆O₃₈

C₈₄H₁₁₈N₁₆O₃₅

C₈₇H₁₂₀N₁₆O₃₃

C₈₉H₁₂₃N₁₅O₃₄

Refernces

• 1、 Ibatullin, Farid M.,Selivanov, Stanislav I.. "Reaction of N-Fmoc aspartic anhydride with glycosylamines: a simple entry to N-glycosyl asparagines". . p. 6351 - 6354. Retrieved 2009.
• 2、 Berthet, Mathéo,Davanier, Florian,Dujardin, Gilles,Martinez, Jean,Parrot, Isabelle. "MgI2-Mediated Chemoselective Cleavage of Protecting Groups: An Alternative to Conventional Deprotection Methodologies". supporting information. p. 11014 - 11016. Retrieved 2015/11/10.
• 3、 Weis, Simone,Shafiq, Zahid,Gropeanu, Radu A.,Del Campo, Aránzazu. "Ethyl substituted coumarin-4-yl derivatives as photoremovable protecting groups for amino acids with improved stability for SPPS". scheme or table. p. 52 - 57. Retrieved 2012/09/07.