FMOC-LYS(IVDDE)-OH

Base Information

• Chemical Name: FMOC-LYS(IVDDE)-OH
• CAS No.: 204777-78-6
• Molecular Formula: C34H42N2O6
• Molecular Weight: 574.717
• Hs Code.: 2924 29 70
• Mol file: 204777-78-6.mol

Synonyms:N-a-Fmoc-N-e-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-lysine;Nalpha-Fmoc-Nepsilon-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl]-L-lysine;Fmoc-lysine(ivdde)-oh;fmoc-lys(ivdde)-OH;Fmoc-Lys(Ddiv)-OH;

Chemical Property of FMOC-LYS(IVDDE)-OH

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 765.609 °C at 760 mmHg
• PKA: 3.88±0.21(Predicted)
• Flash Point: 416.826 °C
• PSA: 121.80000
• Density: 1.183 g/cm³
• LogP: 6.77840
• Storage Temp.: 2-8°C

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-Lys(Ddiv)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Fmoc-lys(IVDDE)-OH is a kind of FMOC (9H-fluoren-9-ylmethoxycarbon) and N-IVDDE (1-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-3-methyl-butyl) double protected amino acid (lysine). It is important during peptide manufacturing. It is mainly used for the production of peptides which required to be modified on the Lysine side chain, including peptides labeled peptides, PEGylated peptides or peptides cyclized through the Lys side chain. It can also be used for the manufacturing of anionic cell penetrating peptide which is useful for intracellular delivery of therapeutic agents such as proteins and nucleic acids. The IVDDE group can be conveniently removed thorough hydrazine in the presence of acid labile groups.
• Uses: ivDde = 1-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-3-methyl-butyl The ivDde protective group possesses higher orthogonality regarding Boc and Fmoc in comparison to Dde. Fmoc-Lys(Ddiv)-OH is orthogonally protected lysine. The Ddiv protection is stable to piperidine. Fmoc-Lys(ivDde)-OH is especially useful for preparing peptides selectively modified on the Lys sidechain, such as peptides labeled peptides, PEGylated peptides or peptides cyclized through the Lys sidechain. The ivDde protective group possesses higher orthogonality regarding Boc and Fmoc in comparison to Dde. The ivDde group can be selectively removed with hydrazine in the presence of acid labile groups such as t-butyl and trityl based protecting groups.

Technology Process of FMOC-LYS(IVDDE)-OH

There total 4 articles about FMOC-LYS(IVDDE)-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: 64.0%

Fmoc-Lys-OH (105047-45-8) + 2-(1-hydroxy-3-methylbutylidene)-5,5-dimethylcyclohexane-1,3-dione (172611-72-2) → Fmoc-Lys(ivDde)-OH (204777-78-6)

Guidance literature:

With trifluoroacetic acid; In ethanol; for 60h; Heating;

DOI:10.1016/S0040-4039(97)10828-0

Reference yield:

Fmoc-Lys(ivDde)-Wang resin → Fmoc-Lys(ivDde)-OH (204777-78-6)

Guidance literature:

With 2-(2-nitrophenyl)propoxycarbonyl hydrazine; In DMF (N,N-dimethyl-formamide); for 3h; not specified Reactivity; Agitating in the dark;

Reference yield:

3-methylbutyric acid (503-74-2) → Fmoc-Lys(ivDde)-OH (204777-78-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC, DMAP

2: 64 percent / TFA / ethanol / 60 h / Heating

With dmap; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol;

DOI:10.1016/S0040-4039(97)10828-0

upstream raw materials:

Fmoc-Lys-OH

2-(1-hydroxy-3-methylbutylidene)-5,5-dimethylcyclohexane-1,3-dione

3-methylbutyric acid

dimedone

Refernces

• 1、 Chhabra, Siri Ram,Hothi, Bhupinder,Evans, David J.,White, Peter D.,Bycroft, Barrie W.,Chan, Weng C.. "An appraisal of new variants of Dde amine protecting group for solid phase peptide synthesis". . p. 1603 - 1606. Retrieved 2007/10/03.