1190-48-3

Basic information

• Product Name: N-EPSILON-FORMYL-L-LYSINE
• Synonyms: EPSILON-FORMYL-L-LYSINE;H-LYS(FOR)-OH;H-LYS(CHO)-OH;N-EPSILON-FORMYL-L-LYSINE;N(epsilon)-formyllysine;NE-FORMYL-L-LYSINE;N6-Formyl-L-lysine;-Formyl-L-lysine
• CAS NO: 1190-48-3
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• Product Categories: A - H;Amino Acids;Modified Amino Acids
• Mol File: 1190-48-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 438.5 °C at 760 mmHg
• Flash Point: 219 °C
• Appearance: /
• Density: 1.169 g/cm³
• Vapor Pressure: 6.46E-09mmHg at 25°C
• Refractive Index: 3 ° (C=0.9, H2O)
• CAS DataBase Reference: N-EPSILON-FORMYL-L-LYSINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-EPSILON-FORMYL-L-LYSINE(1190-48-3)
• EPA Substance Registry System: N-EPSILON-FORMYL-L-LYSINE(1190-48-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1190-48-3(Hazardous Substances Data)

Usage

Description

N-Epsilon-formyl-L-lysine, a non-proteinogenic L-alpha-amino acid, is the N6-formyl derivative of L-lysine. It serves as a pyrrolysine analog and is utilized as a substrate for pyrrolysyl-tRNA synthetase.

Uses

Used in Pharmaceutical Industry:
N-Epsilon-formyl-L-lysine is used as a precursor in the preparation of derivatives of the Triterpene enfumafungin. These derivatives are employed for their therapeutic use as antifungal agents, targeting and inhibiting the growth of various fungi.
Additionally, N-Epsilon-formyl-L-lysine is used as a substrate in the development of (1,3)-β-D-Glucan synthase inhibitors. These inhibitors play a crucial role in the medical field by targeting specific enzymes involved in the synthesis of glucans, which are essential for the cell wall structure of fungi. This inhibition can lead to the disruption of fungal growth and pathogenicity, making it a valuable tool in the treatment of fungal infections.

InChI:InChI=1/C7H14N2O3/c8-6(7(11)12)3-1-2-4-9-5-10/h5-6H,1-4,8H2,(H,9,10)(H,11,12)/t6-/m0/s1

Upstream product

• 56-87-1 L-lysine 
• 109-94-4 formic acid ethyl ester 
• 146039-03-4 N-(Diethylcarbamoyl)-N-methoxyformamide 
• 657-27-2 L-Lysine hydrochloride 
• 2483-47-8 N^α-Boc-N^ε-formyl-L-lysine 
• 13734-28-6 Boc-Lys-OH 
• 70-53-1 2,6-diaminohexanoic acid hydrochloride 
• 79-01-6 Trichloroethylene 
• 67427-39-8 For-DL-Lys(-For)-OH 

Downstream Products

• 2483-47-8 N^α-Boc-N^ε-formyl-L-lysine 
• 20807-05-0 Z-Lys(For)-OH 
• 77663-90-2 (S)-6-Formylamino-2-(3,4,5-trimethoxy-thiobenzoylamino)-hexanoic acid 
• 3105-95-1 pipecolinic acid 
• 77663-91-3 N^α-(3,4,5-trimethoxythiobenzoyl)lysine 
• 77663-98-0 4,5-Dihydro-5-oxo-2-(3,4,5-trimethoxyphenyl)-4-thiazolebutylamine dihydrobromide 
• 100952-02-1 Nε-Formyl-Nα-benzyloxycarbonyl-L-lysin-amid 
• 103757-40-0 Z-Lys(CHO)-Lys(CHO)-NH₂ 
• 111438-77-8 Z-Lys(CHO)-Lys(CHO) 
• 114792-28-8 Z-Lys(CHO)-Lys(CHO)-OMe 

Relevant articles and documents

Degradation of 1-deoxy-d-erythro-hexo-2,3-diulose in the presence of lysine leads to formation of carboxylic acid amides

A novel species of amides formed from degradation of one of the most important key intermediates in Maillard hexose chemistry-1-deoxyhexo-2,3- diulose-was investigated. In 1-deoxyhexo-2,3-diulose/Nα-t-BOC- lysine reaction mixtures four amides, Nε-acetyl lysine, N ε-formyl lysine, Nε-lactoyl lysine and N ε-glycerinyl lysine, were identified and their structures verified by authentic reference standards. Amides and corresponding carboxylic acids (acetic acid, formic acid, lactic acid and glyceric acid) accumulated over time. Both Nε-lysine amides and carboxylic acids were thus determined as stable Maillard end products. Results of model incubations suggested the synthesis of amides to be mechanistically closely related to the formation of their corresponding carboxylic acids by β-dicarbonyl cleavage. Due to the different chemical properties of all the compounds monitored, various analytical strategies had to be carried out (LC-MS2, GC-MS, GC-FID, enzymatic determination).

A new formylating reagent: N-(diethylcarbamoyl)-N-methoxyformamide

A simple and efficient method for the direct chemoselective formylation of primary amines in the presence of alcohols or secondary amines using a new reagent, N-(diethylcarbamoyl)-N-methoxyformamide is described.