Fmoc-D-Asp-OH

Base Information

• Chemical Name: Fmoc-D-Asp-OH
• CAS No.: 136083-57-3
• Molecular Formula: C₁₉H₁₇NO₆
• Molecular Weight: 355.347
• Hs Code.: 29225090
• European Community (EC) Number: 808-544-8
• DSSTox Substance ID: DTXSID60426525
• Nikkaji Number: J2.650.778B
• Wikidata: Q72477998
• Mol file: 136083-57-3.mol

Synonyms:Fmoc-D-Asp-OH;136083-57-3;Fmoc-D-aspartic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-aspartic Acid;N-Fmoc-D-aspartic Acid;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioic acid;MFCD01318740;SCHEMBL1486199;DTXSID60426525;AKOS015840857;AM81589;CS-W011842;HY-W011126;AC-17110;DS-15024;F0592;EN300-81381;A886878;J-300073;Q-101797;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanedioic acid;(R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)SUCCINIC ACID;(2R)-2-{[(9H-Fluoren-9-ylmethoxy)carbonyl]amino}butanedioic acid, AldrichCPR

Chemical Property of Fmoc-D-Asp-OH

Chemical Property:

• Refractive Index: 29 ° (C=1, DMF)
• Boiling Point: 587.21 °C at 760 mmHg
• PKA: 3.66±0.23(Predicted)
• Flash Point: 308.933 °C
• PSA: 112.93000
• Density: 1.4 g/cm³
• LogP: 2.84390
• Storage Temp.: Store at RT.
• 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:

98%,99%, ^*data from raw suppliers

N-Fmoc-D-asparticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F
• Hazard Codes: Xn,F
• 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-D-aspartic acid is an N-Fmoc-protected form of D-Aspartic acid (A790020). D-Aspartic acid is the unnatural isomer of L-Aspartic acid (A790024). D-Aspartic acid naturally occurs in human ovarian follicular fluid, and is thought to be linked to oocyte quality. It is also found in the white matter of human brains, more specifically in myelin proteins.

Technology Process of Fmoc-D-Asp-OH

There total 17 articles about Fmoc-D-Asp-OH 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:

Fmoc-Asn(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxazolidinone

C₃₄H₃₆N₂O₁₄

C₅₄H₄₄N₂O₁₄

C₄₆H₅₂N₂O₂₂

Refernces

• 1、 Palladino, Pasquale,Stetsenko, Dmitry A.. "New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: Dilute HCl in fluoro alcohol". supporting information. p. 6346 - 6349. Retrieved 2013/02/25.
• 2、 Singh, Suneel P.,Michaelides, Alex,Merrill, A. Rod,Schwan, Adrian L.. "A microwave-assisted synthesis of (S)-N-protected homoserine γ-lactones from l-aspartic acid". experimental part. p. 6825 - 6831. Retrieved 2011/10/08.