PHI90001

D-Ser(8)-Liraglutide

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

• Synonym(s): D-Ser(14)-Liraglutide [GLP-1 numbering], H-His-Ala-Glu-Gly-Thr-Phe-Thr-D-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Lys(γ-Glu-palmitoyl)-Glu-Phe-Ile-Ala-Trp-Leu-Val-Arg-Gly-Arg-Gly-OH
• Empirical Formula (Hill Notation): C₁₇₂H₂₆₅N₄₃O₅₁
• Molecular Weight: 3751.20
• UNSPSC Code: 41116107

Properties

• grade: analytical standard
• Quality Segment: 100
• API family: liraglutide, liraglutide, liraglutide, liraglutide
• form: powder, solid
• 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](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](N)CC1=CNC=N1)=O)C)=O)CCC(O)=O)=O)=O)[C@@H](C)O)=O)CC2=CC=CC=C2)=O)[C@@H](C)O)=O)CO)=O)CC(O)=O)=O)C(C)C)=O)CO)=O)C(N[C@H](C(N[C@H](C(N[C@H](C(NCC(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CCC(O)=O)C(N[C@@H](CC3=CC=CC=C3)C(N[C@H](C(N[C@@H](C)C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(NCC(N[C@@H](CCCNC(N)=N)C(NCC(O)=O)=O)=O)=O)=O)C(C)C)=O)CC(C)C)=O)CC4=CNC5=CC=CC=C45)=O)=O)[C@H](CC)C)=O)=O)=O)CCCCNC(CC[C@H](NC(CCCCCCCCCCCCCCC)=O)C(O)=O)=O)=O)C)=O)C)=O)CCC(N)=O)=O)=O)CCC(O)=O)=O)CC(C)C)=O)CC6=CC=C(C=C6)O)=O

Description

General description

The analytical standard of D-Ser(8)-Liraglutide is a stereoisomeric impurity of Liraglutide in which the L-Serine residue at position 8, API numbering (and position 14 in GLP-1 numbering) is replaced by its D-enantiomer (D-Ser). This single chiral inversion, two residues from the N-terminus, can arise during solid-phase peptide synthesis (SPPS) through incomplete chiral control or racemisation under acidic/basic coupling conditions. The compound retains the full 31-residue backbone of Liraglutide and carries the characteristic palmitoyl–γGlu–Lys26 fatty acid conjugate responsible for albumin binding and extended half-life. However, the D-amino acid substitution is expected to locally distort the α-helical secondary structure, potentially altering GLP-1 receptor binding affinity and metabolic stability.

Application

Used as an analytical standard for the identification and semi-quantification of the D-Ser-8 stereoisomeric impurity in Liraglutide API by reversed-phase HPLC, chiral chromatography, and LC-MS/MS methods.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Codes: H361d
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable