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Merck
CN

SMB01416

Fructoselysine hydrochloride

new

≥95%

Synonym(s):

ε-Fructoselysine, ε-N-Deoxyfructosyllysine, Nε-(1-Deoxy-D-fructos-1-yl)-L-lysine, Fructosyllysine

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About This Item

Empirical Formula (Hill Notation):
C12H24N2O7 · xHCl
CAS Number:
21291-40-7
Molecular Weight:
308.33 (free base basis)
MDL number:
MFCD28167702

Key Documents

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biological source

synthetic

Quality Level

100

Assay

≥95%

form

powder

color

faint yellow to yellow, to beige

bp

654.5 °C ((Predicted) (Pressure: 760.00 Torr))

solubility

DMF: soluble
DMSO: soluble
methanol: soluble

application(s)

general analytical
life science and biopharma
metabolomics

storage temp.

−20°C

SMILES string

C([C@H]([C@@H]([C@@H](CO)O)O)O)(CNCCCC[C@@H](C(O)=O)N)=O

InChI

InChI=1S/C12H24N2O7/c13-7(12(20)21)3-1-2-4-14-5-8(16)10(18)11(19)9(17)6-15/h7,9-11,14-15,17-19H,1-6,13H2,(H,20,21)/t7-,9+,10+,11+/m0/s1

InChI key

BFSYFTQDGRDJNV-AYHFEMFVSA-N

General description

Fructoselysine, also known as Fructosyl-lysine, is an important glyco-amino acid formed through the non-enzymatic glycation of lysine with glucose via the Maillard reaction. As an Amadori product, it is a foundational intermediate in the development of advanced glycation end products (AGEs), compounds associated with aging, diabetes, and other chronic conditions.
This compound plays a crucial role in research on protein glycation, food chemistry, and metabolic disorders. Fructoselysine is also a precursor to glucosepane, a lysine-arginine protein cross-link used as a biomarker in diabetes detection. Its diverse biological and chemical properties make it invaluable for understanding glycation processes and their impact on human health.

Application

Fructoselysine could find application in: Protein Glycation Studies: Serves as a model system for investigating glycation reactions involving lysine, amino acids, and fatty acids.

Diabetes Research: A precursor to glucosepane, providing insights into diabetes-related protein modifications and AGE formation.

Food Chemistry: A marker for the Maillard reaction during food heating, contributing to flavor and browning while signaling nutritional changes.

Features and Benefits

Versatile and adaptable for wide variety of research and metabolomics applications.

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000451731
0000451731

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