Saccharopine hydrochloride

• CAT Number: I042337
• Molecular Formula: C11H21ClN2O6
• Molecular Weight: 312.75
• Purity: ≥95%
• Synonyms: (2S)-2-[[(5S)-5-amino-5-carboxypentyl]amino]pentanedioic acid;hydrochloride
• InChI: InChI=1S/C11H20N2O6.ClH/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15;/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19);1H/t7-,8-;/m0./s1
• InChIKey: UAWUYRUBRIPRNY-WSZWBAFRSA-N
• SMILES: C(CCNC(CCC(=O)O)C(=O)O)CC(C(=O)O)N.Cl

Saccharopine (L-Saccharopine) hydrochloride, a lysine degradation intermediate, is a mitochondrial toxin. Lysine and α-ketoglutarate are converted into Saccharopine hydrochloride by the lysine-ketoglutarate reductase. Saccharopine hydrochloride is then oxidized to α-aminoapidate semialdehyde and glutamate by the saccharopine dehydrogenase. Saccharopine hydrochloride impairs development by disrupting mitochondrial homeostasis[1][2][3].
Saccharopine accumulation leads to mitochondrial damage and functional loss which is induced by saccharopine dehydrogenase (SDH) mutations of α-aminoadipate semialdehyde synthase (AASS)-1 in C. elegans[1].
Saccharopine accumulation induces mitochondrial damage and progressive postnatal growth retardation in Aass mutant mice[1].

Reference

[1]. Zhou J, et, al. The lysine catabolite saccharopine impairs development by disrupting mitochondrial homeostasis. J Cell Biol. 2019 Feb 4;218(2):580-597.
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[2]. Leandro J, et, al. Saccharopine, a lysine degradation intermediate, is a mitochondrial toxin. J Cell Biol. 2019 Feb 4;218(2):391-392.
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[3]. Papes F, et, al. Lysine degradation through the saccharopine pathway in mammals: involvement of both bifunctional and monofunctional lysine-degrading enzymes in mouse. Biochem J. 1999 Dec 1;344 Pt 2(Pt 2):555-63.
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