75932-02-4

Basic information

• Product Name: N-α,N-ε-di-Fmoc-D-lysine
• Synonyms: N-α,N-ε-di-Fmoc-D-lysine;N-a,N-e-di-Fmoc-D-lysine;N-.ALPHA.,N-.EPSILON.-DI-FMOC-D-LYSINE;(R)-1,13-di(9H-fluoren-9-yl)-3,11-dioxo-2,12-dioxa-4,10-diazatridecane-5-carboxylic acid;D-Lysine, N2,N6-bis[(9H-fluoren-9-ylMethoxy)carbonyl]-;FMoc-D-Lys(FMoc)-OH N-α,N-ε-di-FMoc-D-lysine;N2,N6-Bis-FMoc-D-lysine;N2,N6-Bis[(9H-fluoren-9-ylMethoxy)carbonyl]lysine
• CAS NO: 75932-02-4
• Molecular Formula: C₃₆H₃₄N₂O₆
• Molecular Weight: 590.673
• Mol File: 75932-02-4.mol

Chemical Properties

• Melting Point: ～130°C
• Appearance: /Solid
• Storage Temp.: Store at 0-5°C
• CAS DataBase Reference: N-α,N-ε-di-Fmoc-D-lysine(CAS DataBase Reference)
• NIST Chemistry Reference: N-α,N-ε-di-Fmoc-D-lysine(75932-02-4)
• EPA Substance Registry System: N-α,N-ε-di-Fmoc-D-lysine(75932-02-4)

Safety Data

• Hazardous Substances Data: 75932-02-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Upstream product

• 56-87-1 L-lysine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 657-27-2 L-Lysine hydrochloride 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 28920-44-7 (9H-fluoren-9-yl)methyl azidoformate 
• 7274-88-6 D-lysine hydrochloride 

Downstream Products

• 439286-58-5 (S)-2,6-Diamino-hexanoic acid {2-[2-(2,4-dichloro-phenoxy)-acetylamino]-ethyl}-amide 
• 745795-93-1 N-(N^α,N^ε-bis-Fmoc-L-Lys)-O-(4,4'-dimethoxytrityl)-O'-(tert-butyldimethylsilyl)diethanolamine 

Relevant articles and documents

New conjugates of antitumor antibiotic doxorubicin with water-soluble galactomannan: Synthesis and biological activity

New water-soluble conjugates in the form of Schiff bases (DGM-1 and DGM-2) were prepared by the interaction of water-soluble periodate-oxidized galactomannan with doxorubicin or N-(L-lysyl)doxorubicin, respectively. The water-soluble galactomannan (DAVANAT, a commercial product of Pro-Pharmaceuticals company) was obtained by partial acidic hydrolysis of high-molecular-mass galactomannan from Cyamopsis tetragonoloba (guar gum) seeds. The conjugate stability was studied in aqueous solutions. The DGM-1 anti-proliferative activity was comparable with that of doxorubicin on three models: cell lines of murine melanoma B16-F1 and human breast cancer MCF-7 (HTB-22) and human colon cancer HT-29 (HTB-38). DGM-2 was poorly active in all the three tests. DGM-1 can thus be regarded as a high-molecular-mass depot form of doxorubicin.

Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin

Sialin, encoded by the SLC17A5 gene, is a lysosomal sialic acid transporter defective in Salla disease, a rare inherited leukodystrophy. It also enables metabolic incorporation of exogenous sialic acids, leading to autoantibodies against N-glycolylneuraminic acid in humans. Here, we identified a novel class of human sialin ligands by virtual screening and structure-activity relationship studies. The ligand scaffold is characterized by an amino acid backbone with a free carboxylate, an N-linked aromatic or heteroaromatic substituent, and a hydrophobic side chain. The most potent compound, 45 (LSP12-3129), inhibited N-acetylneuraminic acid 1 (Neu5Ac) transport in a non-competitive manner with IC50 ≈ 2.5 μM, a value 400-fold lower than the KM for Neu5Ac. In vitro and molecular docking studies attributed the non-competitive character to selective inhibitor binding to the Neu5Ac site in a cytosol-facing conformation. Moreover, compound 45 rescued the trafficking defect of the pathogenic mutant (R39C) causing Salla disease. This new class of cell-permeant inhibitors provides tools to investigate the physiological roles of sialin and help develop pharmacological chaperones for Salla disease.

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