PHI90004

D-Glu-(17)-Liraglutide

GLP-1 Agonist Impurity, analytical standard, Numbering in the name as per API

• Synonym(e): D-Glu-(23)-Liraglutide, H-His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-D-Glu-Ala-Ala-Lys (γ-Glu-Palmitoyl)-Glu-Phe-Ile-Ala-Trp-Leu-Val-Arg-Gly-Arg-Gly-OH
• Empirische Formel (Hill-System): C₁₇₂H₂₆₄N₄₂O₅₂
• Molekulargewicht: 3752.19
• UNSPSC Code: 41116107

Eigenschaften

• grade: analytical standard
• Quality Segment: 100
• API family: liraglutide, liraglutide, liraglutide, liraglutide
• form: powder
• technique(s): HPLC: suitable, LC/MS: suitable, liquid chromatography (LC): suitable, mass spectrometry (MS): suitable
• color: white to off-white
• format: neat
• storage temp.: −20°C
• SMILES string: OC[C@@H](C(N[C@@H](CC1=CC=C(O)C=C1)C(N[C@@H](CC(C)C)C(N[C@@H](CC C(O)=O)C(NCC(N[C@H](CCC(O)=O)C(N[C@@H](C)C(N[C@@H](C)C(N[C@@H](CCCCNC(CC [C@@H](C(O)=O)NC(CCCCCCCCCCCCCCC)=O)=O)C(N[C@H](C(N[C@H](C(N [C@@H]([C@@H](C)CC)C(N[C@H](C(N[C@@H](CC2=CNC3=CC=CC=C23)C(N[C@@H](CC(C) C)C(N[C@@H](C(C)C)C(N[C@H](C(NCC(N[C@H](C(NCC(O)=O)=O)CCCNC( N)=N)=O)=O)CCCNC(N)=N)=O)=O)=O)=O)C)=O)=O)CC4=CC=CC=C4)=O)CCC(O)=O)=O)=O )=O)=O)=O)=O)=O)=O)=O)NC([C@H](CO)NC([C@H](C(C)C)NC([C@H](CC (O)=O)NC([C@H](CO)NC([C@H]([C@H](O)C)NC([C@H](CC5=CC=CC=C5)N C([C@H]([C@H](O)C)NC(CNC([C@H](CCC(O)=O)NC([C@H](C)NC([C@H](CC6=CNC=N6)N )=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O

Beschreibung

General description

D-Glu(17)-Liraglutide is a stereoisomeric impurity of Liraglutide characterised by the replacement of L-Glutamic acid at position 17 (API numbering; position 17 in GLP-1 numbering) with its D-enantiomer (D-Glu). Position 17 resides within the central α-helical domain of the peptide, and its stereoinversion may perturb helix stability and receptor contact surface. The impurity is otherwise structurally identical to Liraglutide, retaining the palmitoyl–γGlu–Lys26 fatty acid conjugate. Racemisation at Glu residues during SPPS, particularly under prolonged activation or elevated temperature, is a recognised source of this impurity type.

Application

Used as an analytical standard for the identification and semi-quantification of the D-Glu17 diastereomeric impurity in Liraglutide API by reversed-phase HPLC, chiral chromatography, and LC-MS/MS methods.

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable