L-Saccharopine

• CAS: 997-68-2
• Catalog Number: ACM997682
• Category: Other Products; Main Products
• Molecular Weight: 276.29
• Molecular Formula: C₁₁H₂₀N₂O₆
• Synonyms: L-SACCHAROPINE; L-Saccharopine
• IUPAC Name: (2S)-2-[[(5S)-5-amino-6-hydroxy-6-oxohexyl]amino]pentanedioic acid
• SMILES: C(CCNC(CCC(=O)O)C(=O)O)CC(C(=O)O)N
• InChI Key: ZDGJAHTZVHVLOT-YUMQZZPRSA-N
• Boiling Point: 537.2ºC at 760mmHg
• Melting Point: >234 °C
• Flash Point: 278.7ºC
• Density: 1.333g/cm³
• Appearance: White solid
• Exact Mass: 276.13200
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• WGK Germany: 3

Case Study

L-Saccharopine as a Potential Diagnostic Biomarker for Pituitary Stalk Interruption Syndrome

Guo, Ye, et al. Orphanet Journal of Rare Diseases 17.1 (2022): 267.

Pituitary stalk interruption syndrome (PSIS) is a rare congenital disorder characterized by anatomical defects of the pituitary gland, leading to growth and pubertal development abnormalities.This study employed untargeted metabolomics and lipidomics profiling of seminal plasma to identify molecular signatures of PSIS and potential diagnostic biomarkers.
Methods: Seminal plasma samples from 21 PSIS patients and 23 healthy controls were analyzed using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS). Differential metabolites were identified through orthogonal projections to latent structures-discriminant analysis (OPLS-DA) and receiver operating characteristic (ROC) analysis.
Key Results:
Metabolomic profiling revealed significantly altered metabolite profiles in PSIS patients compared to healthy controls. Pathway enrichment analysis identified the prolactin signaling pathway and biosynthesis of amino acids as the main differentially modified pathways. L-Saccharopine, an intermediate in lysine metabolism, was among the significantly altered metabolites in PSIS patients.
Combined ROC analysis using L-saccharopine and pregnenolone sulfate demonstrated excellent diagnostic performance for PSIS, with an area under the curve (AUC) of 0.927 (95% CI: 0.81-1.00), indicating high sensitivity and specificity for distinguishing PSIS patients from healthy controls.
L-Saccharopine thus serves as a promising metabolite biomarker for PSIS diagnosis, contributing to a dual-marker panel with high discriminatory power for this rare endocrine disorder.

L-Saccharopine as a Key Metabolite Linking High-Fat Diet-Induced Gut Microbiota Dysbiosis to Ovarian Dysfunction

Wen, Jingyi, et al. Gut Microbes 16.1 (2024): 2412381.

High-fat diet (HFD) is a significant public health concern linked to obesity and various metabolic disorders, including female infertility. This study investigated the role of gut microbiota dysbiosis and identified L-saccharopine as a critical metabolite mediating HFD-induced ovarian dysfunction.
Female mice were administered HFD at different developmental stages (pre-puberty, post-puberty, young adult, middle age). Fecal microbiota transplantation (FMT) from HFD donors to normal diet recipients was performed. Untargeted and targeted metabolomics analyses identified L-saccharopine as a key metabolite enriched in feces, serum, and ovaries of HFD and HFD-FMT mice. In vitro and in vivo experiments examined its effects on granulosa cells and oocytes.
Key Findings:
· Untargeted metabolomics identified L-saccharopine as the most significantly upregulated metabolite in HFD feces (VIP score highest). Targeted quantification confirmed its elevation in serum and ovaries of HFD and HFD-FMT mice, correlating positively with Clostridiales abundance.
· In mouse granulosa cells, L-saccharopine (100 nM, 48 h) inhibited E2 synthesis, downregulated CYP19A1/HSD17B1, reduced mitochondrial number and ATP production, decreased mitochondrial membrane potential, and inhibited AMPKa/MFF phosphorylation-blocking mitochondrial fission.
· In oocytes, L-saccharopine reduced GVBD and polar body extrusion rates, increased spindle/chromosome abnormalities, elevated ROS, and decreased MMP. The AMPKa activator AICAR rescued these effects both in vitro and in vivo.
· In vivo, L-saccharopine (2.5 mg/kg/d, 6 weeks) reduced serum E2 and AMH, decreased primordial follicles and corpora lutea, increased atretic follicles, and impaired fertility-phenocopying HFD-FMT effects.