Fmoc-Lys(Ddiv)-OH

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.

Chemical properties

White to pale yellow powder

The Uses of Fmoc-Lys(Ddiv)-OH

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.

The Uses of Fmoc-Lys(Ddiv)-OH

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.

Advantages

Fmoc-Lys(ivDde)-OH could be used to synthesize hetero-branched peptidesto avoid homodimer generation and construct heterodimers with a high ratio. This agent was used to generate Cellpenetrating peptides (CPP) and candidate peptides in one molecule[1].

References

Wen-Qu, L. I., X. U. Hong-Yan, and L. I. Zhan-Xiong. "Synthesis of End N-Ivdde Protected Amino Acid."Chinese Journal of Synthetic Chemistry 17.2(2009):213-215.
http://www.chempep.com/ChemPep_Products2_Fmoc-Amino-Acid.php?id=101224
Chen, Hui Ting, et al. "Anionic cell penetrating peptide and its use for intracellular delivery." US, US8614194. 2013.
[1] Kozaki L, et al. Disulfide linked hetero dimeric peptide arrays for screening functional peptides inside cells. Journal of Bioscience and Bioengineering, 2019; 129: 613-618.