FMOC-LYS(BOC)(ME)-OH

Base Information

• Chemical Name: FMOC-LYS(BOC)(ME)-OH
• CAS No.: 951695-85-5
• Molecular Formula: C27H34N2O6
• Molecular Weight: 482.577
• Hs Code.: 2924 29 70
• Mol file: 951695-85-5.mol

Synonyms:Fmoc-Lys(Boc,Me)-OH;Fmoc-Lys(Me,Boc)-OH;

Chemical Property of FMOC-LYS(BOC)(ME)-OH

Chemical Property:

• Melting Point: 85-87 °C
• Boiling Point: 665.36 °C at 760 mmHg
• PKA: 3.88±0.21(Predicted)
• Flash Point: 356.197 °C
• PSA: 105.17000
• Density: 1.2 g/cm³
• LogP: 5.40640
• Storage Temp.: -15°C

Purity/Quality:

≥97%,≥99%, ^*data from raw suppliers

Fmoc-lys(me,boc)-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Description: Fmoc-lys (BOC) (ME)-OH is a kind of protected form of lysine. Lysine is double-protected by butyloxycarbonyl (BOC) and 9H-fluoren-9-ylmethoxycarbon (FMOC). It is a derivative for the introduction of monomethyl-lysine during Fmoc SPPS. Coupling can be carried out using any standard activation method. The Boc protecting group can be removed through the TFA-mediated cleavage reaction. As a kind of protected amino acid, it is an important intermediate in various fields such as peptide synthesis, asymmetric synthesis, medicinal chemistry as well as polymer chemistry.
• Uses: Heterochromatin protein 1 (HP1) depends on trimethylation of H3 Lys 9; aggregation of chromatines depends on Lys methylation Fmoc-Lys(Boc, Me)-OH is useful for preparing monomethylated histone fragments utilized in studying the regulatory roles of methylated histones. Fmoc-Lys(Boc,Me)-OH can be coupled using standard activating procedures. The Boc group on the side epsilon nitrogen atom is removed with TFA, usually at the same time as the peptide is cleaved from the resin. Fmoc-Lys(Boc, Me)-OH is a novel derivative for the introduction of monomethyl-lysine during Fmoc SPPS. Coupling can be carried out using any standard activation method. Removal of the Boc protecting group occurs during the course of the TFA-mediated cleavage reaction.

Technology Process of FMOC-LYS(BOC)(ME)-OH

There total 17 articles about FMOC-LYS(BOC)(ME)-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: 84.0%

N2-Fmoc-N6-Boc-N6-monomethyl-4,5-(E)-dehydrohexanoic acid → Νε-tert-butoxycarbonyl-Να-(9-fluorenylmethoxycarbonyl)-Νε-methyllysine (951695-85-5,2044709-77-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃;

DOI:10.1021/acschembio.5b00738

Reference yield: 80.0%

Nε-tert-butyl-oxycarbonyl-Nε-methyl-L-lysine (1190081-84-5) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Νε-tert-butoxycarbonyl-Να-(9-fluorenylmethoxycarbonyl)-Νε-methyllysine (951695-85-5,2044709-77-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; pH=Ca. 10;

DOI:10.1007/s00726-014-1690-6

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + N-fluorenylmethoxycarbonyl-N'-methyl-L-lysine (951695-86-6) → Νε-tert-butoxycarbonyl-Να-(9-fluorenylmethoxycarbonyl)-Νε-methyllysine (951695-85-5,2044709-77-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 4h; Reagent/catalyst;

upstream raw materials:

N^α-Ac-N^ε-(Boc, methyl)-DL-lysine

N^ε-tert-butyl-oxycarbonyl-N^ε-methyl-L-lysine

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

6-bromo-2-acetamido-2-ethoxycarbonyl-hexanoic acid ethyl ester

Downstream raw materials:

N^ε-(Boc, methyl)-L-lysine-MCA

N^α-Fmoc-N^ε-(Boc, methyl)-L-lysine-MCA

Refernces

• 1、 -. "Preparation method of N epsilon-tert-butoxycarbonyl-N alpha-fluorenylmethoxycarbonyl-N epsilon-methyl-lysine". . . Retrieved 2018/09/08.
• 2、 Chi, Hongfang,Islam, Md. Shahidul,Nsiama, Tienabe K.,Kato, Tamaki,Nishino, Norikazu. "A convenient preparation of N ε-methyl-l-lysine derivatives and its application to the synthesis of histone tail peptides". . p. 1305 - 1311. Retrieved 2014/05/06.