Fmoc-L-4-Pyridylalanine

Base Information

• Chemical Name: Fmoc-L-4-Pyridylalanine
• CAS No.: 169555-95-7
• Molecular Formula: C23H20N2O4
• Molecular Weight: 388.423
• Hs Code.: 29333990
• European Community (EC) Number: 824-668-5
• DSSTox Substance ID: DTXSID10359652
• Wikidata: Q72478869
• Mol file: 169555-95-7.mol

Synonyms:169555-95-7;Fmoc-L-4-Pyridylalanine;FMOC-4-PAL-OH;Fmoc-3-(4-pyridyl)-L-alanine;Fmoc-Ala(4-pyridyl)-OH;Fmoc-L-(4-pyridyl)alanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(pyridin-4-yl)propanoic acid;N-FMOC-3-(4-PYRIDYL)-L-ALANINE;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-pyridin-4-ylpropanoic acid;MFCD00672566;Fmoc-beta-(4-pyridyl)-Ala-OH;Fmoc-D-3-(4-pyridyl)-alanine;FMOC-3-(4-PYRIDYL)-DL-ALANINE;SCHEMBL119545;FMOC-ALA(4-PYRI)-OH;AMY354;Fmoc-3-(4-pyridyl)-Ala-OH;FMOC-4'-PYRIDYL-L-ALA;DTXSID10359652;Fmoc- beta -(4-pyridyl)-Ala-OH;AKOS016843579;AC-9966;CS-W013878;HY-W013162;AS-14758;F0927;EN300-77291;F11943;A811118;J-010558;J-505181;N-Fluorenemethoxycarbonyl-D-3-(4-Pyridyl) Alanine;Fmoc-beta-(4-pyridyl)-Ala-OH, >=97.0% (HPLC);S-169555-95-7;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-(4-pyridyl)-L-alanine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-(4-pyridinyl)-L-alanine;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(pyridin-4-yl)propanoic acid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(PYRIDIN-4-YL)PROPANOIC ACID;2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-pyridyl)propanoic acid;N-Fmoc-3-(4-pyridyl)-L-alanine

Chemical Property of Fmoc-L-4-Pyridylalanine

Chemical Property:

• Vapor Pressure: 1.28E-17mmHg at 25°C
• Melting Point: 219 °C(dec.)
• Refractive Index: 1.637
• Boiling Point: 646.9 °C at 760 mmHg
• PKA: 3.32±0.10(Predicted)
• Flash Point: 345 °C
• PSA: 88.52000
• Density: 1.309 g/cm³
• LogP: 4.00690
• Storage Temp.: 2-8°C
• Solubility.: Soluble in 0.1g in 4mL DMF(clearly soluble).
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 388.14230712
• Heavy Atom Count: 29
• Complexity: 555

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-l-4-pyridylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• 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(CC4=CC=NC=C4)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=NC=C4)C(=O)O
• Uses: Fmoc-?-(4-pyridyl)-Ala-OH is potentially useful for solid phase peptide synthesis techniques.

Technology Process of Fmoc-L-4-Pyridylalanine

There total 8 articles about Fmoc-L-4-Pyridylalanine 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: 65.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-amino-3-(pyridin-4-yl)propanoic acid (37535-49-2) → (S)-N-(9-fluorenylmethoxycarbonyl)-β-(4-pyridyl)alanine (169555-95-7)

Guidance literature:

With sodium carbonate; In water; N,N-dimethyl-formamide; for 0.25h; Ambient temperature;

Reference yield: 40.0%

N-fluorenylmethyloxycarbonyl-4-pyridylalanine-methyl ester (1397697-82-3) → C24H22N2O4 (1397815-20-1) + (S)-N-(9-fluorenylmethoxycarbonyl)-β-(4-pyridyl)alanine (169555-95-7)

Guidance literature:

With ammonium hydroxide; α-chymotrypsine; ammonium acetate; In water; N,N-dimethyl-formamide; at 20 ℃; for 2h; pH=6.9; optical yield given as %ee; Enzymatic reaction;

DOI:10.1007/s00726-010-0829-3

Reference yield:

(4Z)-2-methyl-4((pyridin-4-yl)methylene)oxazol-5(4H)-one (102913-23-5) → C24H22N2O4 (1397815-20-1) + (S)-N-(9-fluorenylmethoxycarbonyl)-β-(4-pyridyl)alanine (169555-95-7)

Guidance literature:

Multi-step reaction with 6 steps

1: water / 100 °C

2: palladium 10% on activated carbon; hydrogen / methanol / 9 h / 20 °C

3: hydrogenchloride; water / 3 h / Reflux

4: sodium hydrogencarbonate / 1,4-dioxane; water / 22 h / 20 °C

5: chloro-trimethyl-silane / 36 h / 40 °C

6: ammonium hydroxide; α-chymotrypsine; ammonium acetate / water; N,N-dimethyl-formamide / 2 h / 20 °C / pH 6.9 / Enzymatic reaction

With hydrogenchloride; ammonium hydroxide; chloro-trimethyl-silane; α-chymotrypsine; palladium 10% on activated carbon; ammonium acetate; water; hydrogen; sodium hydrogencarbonate; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

DOI:10.1007/s00726-010-0829-3

upstream raw materials:

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

(S)-2-amino-3-(pyridin-4-yl)propanoic acid

(4Z)-2-methyl-4((pyridin-4-yl)methylene)oxazol-5(4H)-one

pyridine-4-carbaldehyde

Refernces

• 1、 Andrews, David M.,Gregoriou, Mary,Page, Timothy C. M.,Peach, Josephine M.,Pratt, Andrew J.. "Potential mechanism-based tyrosine kinase inhibitors. Part 2. Design and synthesis of peptides containing heterocyclic tyrosine analogues". . p. 1335 - 1340. Retrieved 2007/10/02.