95464-27-0

Basic information

• Product Name: DL-2-FORMYL-5-(HYDROXYMETHYL)PYRROLE-1-NORLEUCINE
• Synonyms: DL-2-FORMYL-5-(HYDROXYMETHYL)PYRROLE-1-NORLEUCINE
• CAS NO: 95464-27-0
• Molecular Formula: C12H18 N2 O4
• Molecular Weight: 254.28
• Mol File: 95464-27-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DL-2-FORMYL-5-(HYDROXYMETHYL)PYRROLE-1-NORLEUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-FORMYL-5-(HYDROXYMETHYL)PYRROLE-1-NORLEUCINE(95464-27-0)
• EPA Substance Registry System: DL-2-FORMYL-5-(HYDROXYMETHYL)PYRROLE-1-NORLEUCINE(95464-27-0)

Safety Data

• Hazardous Substances Data: 95464-27-0(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 657-27-2 L-Lysine hydrochloride 
• 1404451-31-5 C₃₃H₄₂N₂O₆Si 
• 1404451-32-6 C₂₇H₂₈N₂O₆ 
• 105047-45-8 Fmoc-Lys-OH 
• 1377151-82-0 6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one 
• 178180-79-5 Boc-pyrraline 
• 56-87-1 L-lysine 
• 103880-21-3 dimethyl acetamido-(4-<2-formyl-5-(hydroxymethyl)-1-pyrrol>butyl)malonate 
• 103880-19-9 dimethyl acetamido-<4-(2,5-diformyl-1-pyrrolyl)butyl>malonate 
• 103880-20-2 (+/-)-methyl α-acetamido-2,5-diformylpyrrole-1-hexanoate 
• 103880-14-4 dimethyl acetamido-(4-brombutyl)malonate 
• 103880-18-8 (+/-)-methyl 2-acetamido-6-bromohexanoate 
• 67350-50-9 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde 

Relevant articles and documents

Transport of the Advanced Glycation End Products Alanylpyrraline and Pyrralylalanine by the Human Proton-Coupled Peptide Transporter hPEPT1

The glycation compound pyrraline, which originates from the advanced Maillard reaction, appears in urine after consumption of pyrraline-containlng food. We hypothesized that the absorption of pyrraline occurs In the form of dipeptides rather than the free amino acid. The human Intestinal peptide transporter hPEPT1 was transiently expressed in HeLa cells. In hPEPT1-transfected cells but not in cells transfected with empty vector, the uptake of [14C]glycylsarcosine was strongly inhibited by alanylpyrraline (Ala-Pyrr) and pyrralylalanine (Pyrr-Ala). Free pyrraline did not inhibit peptide uptake. In Xenopus laevis oocytes expressing human PEPT1, both Ala-Pyrr and Pyrr-Ala generated significant inward directed currents. In a third approach, uptake of the dipeptides into hPEPT1 -transfected HeLa cells was analyzed by HPLC. Ala-Pyrr and Pyrr-Ala were taken up by hPEPT1-expressing cells at a 4- to 7-fold higher rate than by HeLa cells transfected with the empty vector. We conclude that pyrraline containing dipeptides are transported by hPEPT1 in an electrogenlc manner into Intestinal cells. 2010 American Chemical Sudety.

Synthesis of monolysyl advanced glycation endproducts and their incorporation into collagen model peptides

The synthesis of advanced glycation endproducts (AGEs), CML, CEL, and pyrraline and their incorporation into collagen model peptides is reported. AGEs are modified amino acids that form on proteins such as collagen and are thought to play a significant role in the pathogenesis of many diseases, particularly diabetes. The synthesis and incorporation of these compounds into synthetic peptides is a key step in developing model systems with which to investigate AGE-modified proteins.

Synthesis of (±)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine. A biologically acitive Maillard reaction product derived from glucose and lysine

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