Z-L-cis-4-hydroxyproline

CAS: 13504-86-4

Ref. 3D-FH48883

Product Information

• Name: Z-L-cis-4-hydroxyproline
• Synonyms: Z-cis-L-Hyp-OH, (2S,4S)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid, (4S)-1-[(benzyloxy)carbonyl]-4-hydroxy-L-proline, (2S,4S)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
• CAS: 13504-86-4

Description

Z-L-cis-4-hydroxyproline is a glycopeptide antibiotic that inhibits the transport of galactose into bacterial cells. It binds to the surface of cells and prevents the uptake of galactose, which is essential for bacterial growth. Z-L-cis-4-hydroxyproline has been shown to inhibit the production of inflammatory cytokines in human macrophages, leading to decreased inflammation and pain.
Z-L-cis-4-hydroxyproline is also chiral and can be synthesized as either a left or right enantiomer. It has been shown that the left form is more potent than the right form, inhibiting cell toxicity better in mice. The left form also has increased uptake by cells and localization in mitochondria as opposed to the right form.

• Brand: Biosynth

Chemical properties

• Molecular weight: 265.26 g/mol
• Formula: C₁₃H₁₅NO₅
• Purity: Min. 95%
• InChI: InChI=1S/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10?,11-/m0/s1
• InChI key: InChIKey=WWVCWLBEARZMAH-DTIOYNMSSA-N
• SMILES: O=C(O)[C@@H]1CC(O)CN1C(=O)OCc1ccccc1