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Fmoc-Nε-dimethyl-L-lysine hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Di-Me L-lysine derivative. The methylation of lysine in histone tails is a common posttranslational modification that functions in histone-regulated chromatin condensation, with binding of methylated lysine occurring in aromatic pockets on chromodomain proteins.

Category

Fmoc-Amino Acids

Catalog number

BAT-003794

CAS number

252049-10-8

Molecular Formula

C23H28N2O4·HCl

Molecular Weight

432.95

Specification
Reference Reading

IUPAC Name

(2S)-6-(dimethylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid;hydrochloride

Synonyms

Fmoc-L-Lys(Me)2-OH HCl; Fmoc-N',N'-dimethyl-L-lysine hydrochloride; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid hydrochloride; (2S)-6-(dimethylamino)-2-(9H-fluoren-9-lmethoxycarbonylamino)hexanoic acid hydrochloride

Appearance

Off-white to light yellow powder

Purity

≥ 98% (HPLC)

Storage

Store at -20 °C

InChI

InChI=1S/C23H28N2O4.ClH/c1-25(2)14-8-7-13-21(22(26)27)24-23(28)29-15-20-18-11-5-3-9-16(18)17-10-4-6-12-19(17)20;/h3-6,9-12,20-21H,7-8,13-15H2,1-2H3,(H,24,28)(H,26,27);1H/t21-;/m0./s1

InChI Key

SJFAFKDBWNFBCC-BOXHHOBZSA-N

Canonical SMILES

CN(C)CCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13.Cl

1. 1-Haloacylpiperazines

S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.

By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.

2. Metal-free and regiospecific synthesis of 3-arylindoles

Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.

A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.