Fmoc-L-Dap(N3)-OH

Base Information

• Chemical Name: Fmoc-L-Dap(N3)-OH
• CAS No.: 684270-46-0
• Molecular Formula: C18H16N4O4
• Molecular Weight: 352.349
• Hs Code.: 2924297099
• European Community (EC) Number: 632-594-8
• DSSTox Substance ID: DTXSID70477785
• Nikkaji Number: J2.737.292I
• Wikidata: Q72444566
• Mol file: 684270-46-0.mol

Synonyms:684270-46-0;Fmoc-L-Dap(N3)-OH;Fmoc-beta-azido-Ala-OH;Fmoc-|A-azido-Ala-OH;Fmoc-L-beta-azidoalanine;(2S)-3-azido-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;(2S)-3-azido-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid;3-Azido-N-Fmoc-L-alanine;Fmoc-Dap(N3)-OH;Fmoc-L-azidoalanine;(S)-3-Azido-2-(Fmoc-amino)propionic acid;Fmoc-Dap(N2)-OH;DTXSID70477785;MFCD11052919;AKOS015940886;AG-G-63082;AM10166;AS-57215;CS-0147244;Fmoc-beta-azido-Ala-OH, >=98.0% (HPLC);Na-Fmoc-Nb-Fmoc-L-2,3-diaminopropionic acid;E70383;EN300-309467;(S)-2-(9-Fluorenylmethyloxycarbonylamino)-3-azidopropanoic acid;(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-AZIDOPROPANOIC ACID

Chemical Property of Fmoc-L-Dap(N3)-OH

Chemical Property:

• Melting Point: >155 (dec.)
• PSA: 128.87000
• LogP: 2.94576
• Storage Temp.: 2-8°C
• Solubility.: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 352.11715500
• Heavy Atom Count: 26
• Complexity: 556

Purity/Quality:

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

Fmoc-L-azidoalanine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CN=[N+]=[N-])C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CN=[N+]=[N-])C(=O)O
• Uses: Fmoc-β-azido-Ala-OH chloride is a general N-terminal protected reagent used in the solid phase peptide synthesis. Azido group allows it to undergo copper-mediated click chemistry reactions.It can be used in:Synthesis of α-N-acetylgalactosamine (α-GalNAc) linked antifreeze glycopeptides (AFGPs).Synthesis of stimuli-responsive multifunctional peptide gatekeepers for drug delivery applications.Synthesis of triazole-linked glycopeptides via Cu(I)-catalyzed 1,3-dipolar cycloaddition (CuAAC).

Technology Process of Fmoc-L-Dap(N3)-OH

There total 9 articles about Fmoc-L-Dap(N3)-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: 88.0%

[2-azido-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (684270-41-5) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid (684270-46-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 8h;

DOI:10.1055/s-2004-817770

Reference yield: 86.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate (108492-14-4,108283-48-3) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid (684270-46-0)

Guidance literature:

tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate; With water; trifluoroacetic acid; In dichloromethane;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1002/psc.2968

Reference yield: 80.0%

3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (181954-34-7) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidopropanoic acid (684270-46-0)

Guidance literature:

With copper(ll) sulfate pentahydrate; triflic azide; sodium hydrogencarbonate; In methanol; dichloromethane; water; at 20 ℃;

DOI:10.1002/psc.2968

upstream raw materials:

[2-azido-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester

(9H-fluoren-9-yl)methyl (S)-(3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate

3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Downstream raw materials:

3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Refernces

• 1、 de Andrade, Peterson,Mantoani, Susimaire P.,Gon?alves Nunes, Paulo Sérgio,Magadán, Carlos Roca,Pérez, Concepción,Xavier, Danilo Jord?o,Hojo, Elza Tiemi Sakamoto,Campillo, Nuria E.,Martínez, Ana,Carvalho, Ivone. "Highly potent and selective aryl-1,2,3-triazolyl benzylpiperidine inhibitors toward butyrylcholinesterase in Alzheimer's disease". . p. 931 - 943. Retrieved 2019/02/14.
• 2、 Wiedmann, Mareike M.,Tan, Yaw Sing,Wu, Yuteng,Aibara, Shintaro,Xu, Wenshu,Sore, Hannah F.,Verma, Chandra S.,Itzhaki, Laura,Stewart, Murray,Brenton, James D.,Spring, David R.. "Development of Cell-Permeable, Non-Helical Constrained Peptides to Target a Key Protein–Protein Interaction in Ovarian Cancer". supporting information. p. 524 - 529. Retrieved 2017/01/07.