Fmoc-L-Lys(Dde)-OH

Base Information

• Chemical Name: Fmoc-L-Lys(Dde)-OH
• CAS No.: 150629-67-7
• Molecular Formula: C31H36N2O6
• Molecular Weight: 532.637
• Hs Code.: 2924 29 70
• Mol file: 150629-67-7.mol

Synonyms:Fmoc-D-Lys(Dde)-OH;

Chemical Property of Fmoc-L-Lys(Dde)-OH

Chemical Property:

• Melting Point: ~80 °C (dec.)
• Boiling Point: 750.1±60.0 °C(Predicted)
• PKA: 3.88±0.21(Predicted)
• PSA: 121.80000
• Density: 1.222±0.06 g/cm3(Predicted)
• LogP: 5.75220
• Storage Temp.: −20°C
• Solubility.: soluble in Methanol

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-lys(dde)-oh ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The amino-protecting group Dde is orthogonal to both Fmoc and Boc protection and therefore useful to enable extension from lysine side chains by using Fmoc-tBu solid-phase methodologies.

Technology Process of Fmoc-L-Lys(Dde)-OH

There total 7 articles about Fmoc-L-Lys(Dde)-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: 70.0%

2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione (94142-97-9) + α-Fmoc-L-lysine hydrochloride (139262-23-0) → Fmoc-Lys(Dde)-OH (150629-67-7)

Guidance literature:

α-Fmoc-L-lysine hydrochloride; With N-ethyl-N,N-diisopropylamine; In water; at 20 ℃;

2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione; With trifluoroacetic acid; In ethanol; water; for 60h; Reflux;

Reference yield: 70.0%

2-acetyldimedone (1755-15-3) + Fmoc-Lys-OH (105047-45-8) → Fmoc-Lys(Dde)-OH (150629-67-7)

Guidance literature:

With triethylamine; In ethanol; for 18h; Reflux;

DOI:10.1021/acs.jmedchem.7b01280

Reference yield: 41.0%

2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione (94142-97-9) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → Fmoc-Lys(Dde)-OH (150629-67-7)

Guidance literature:

Fmoc-Lys(tert-butoxycarbonyl); With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 2h;

2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione; With N-ethyl-N,N-diisopropylamine; In ethanol; for 17h; Reflux;

DOI:10.1016/j.bmc.2016.12.033

upstream raw materials:

2-acetyldimedone

Fmoc-Lys-OH

2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione

dimedone

Refernces

• 1、 -. "ONE-BEAD-TWO-COMPOUND MACROCYCLIC LIBRARY AND METHODS OF PREPARATION AND USE". Paragraph 0160; 0161; 0170. . Retrieved 2018/11/02.
• 2、 Amano, Yuichi,Umezawa, Naoki,Sato, Shin,Watanabe, Hisami,Umehara, Takashi,Higuchi, Tsunehiko. "Activation of lysine-specific demethylase 1 inhibitor peptide by redox-controlled cleavage of a traceless linker". . p. 1227 - 1234. Retrieved 2017/02/05.