Fmoc-Lys(N3)-OH

Base Information

• Chemical Name: Fmoc-Lys(N3)-OH
• CAS No.: 159610-89-6
• Molecular Formula: C21H22N4O4
• Molecular Weight: 394.43
• Hs Code.: 2929900090
• Mol file: 159610-89-6.mol

Synonyms:Fmoc-Lys(N3)-OH

Chemical Property of Fmoc-Lys(N3)-OH

Chemical Property:

• Melting Point: 78 °C(dec.)
• PSA: 128.87000
• LogP: 4.11606
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

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

Fmoc-L-Azidolysine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The side chain azido (N3) group is stable in trifluoroacetic acid or piperidine. It can be readily converted to amine and to synthesis side chain modified peptides and proteins by Solid Phase Peptide Synthesis (SPPS) methodology.

Technology Process of Fmoc-Lys(N3)-OH

There total 10 articles about Fmoc-Lys(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: 94.0%

Fmoc-Lys-OH (105047-45-8) → 6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid (159610-89-6)

Guidance literature:

With copper(ll) sulfate pentahydrate; triflic azide; sodium hydrogencarbonate; In methanol; dichloromethane; water; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201403344

Reference yield: 94.0%

Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → 6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid (159610-89-6)

Guidance literature:

With imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate; In methanol; water; at 20 ℃; pH=8.5;

DOI:10.1039/c2cc35310e

Reference yield: 74.0%

9-fluorenylmethoxycarbonyl-L-alanine hydrochloride (139262-23-0) → 6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid (159610-89-6)

Guidance literature:

With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; copper; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; at 0 - 20 ℃; for 0.0833333h; Flow reactor;

DOI:10.1016/j.tetlet.2015.02.036

upstream raw materials:

Fmoc-Lys-OH

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

(S)-2-amino-6-azidohexanoic acid

imidazole-1-sulfonyl azide hydrochloride

Downstream raw materials:

C₈₄H₁₃₈N₂₂O₂₄

Refernces

• 1、 Hoffknecht, Barbara C.,Worm, Dennis J.,Bobersky, Sandra,Prochnow, Pascal,Bandow, Julia E.,Metzler-Nolte, Nils. "Influence of the Multivalency of Ultrashort Arg-Trp-Based Antimicrobial Peptides (AMP) on Their Antibacterial Activity". . p. 1564 - 1569. Retrieved 2015.
• 2、 Piecyk, Karolina,Jankowska-Anyszka, Marzena. "Chemical conjugation of an mRNA cap analogue with a cell-penetrating peptide as a potential membrane permeable translation inhibitor". . p. 606 - 609. Retrieved 2014.
• 3、 Jetson, Rachael R.,Krusemark, Casey J.. "Sensing Enzymatic Activity by Exposure and Selection of DNA-Encoded Probes". . p. 9562 - 9566. Retrieved 2016.
• 4、 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.
• 5、 Tahoori, Fatemeh,Balalaie, Saeed,Sheikhnejad, Reza,Sadjadi, Mahnaz,Boloori, Parvin. "Design and synthesis of anti-cancer cyclopeptides containing triazole skeleton". . p. 1033 - 1046. Retrieved 2014.
• 6、 Vanhoutte, Roeland,Van De Plassche, Merel A. T.,Verhelst, Steven H. L.. "Rapid Solid-Phase Construction of Serine Hydrolase Probes Results in Selective Activity-Based Probes for Acyl Protein Thioesterases-1/2". . p. 11845 - 11853. Retrieved 2020.