1148-11-4 | Z-Pro-OH

Packsize	Purity	Availability	Price	Discounted Price
25g	98%	in stock	$13.00	$9.00
100g	98%	in stock	$39.00	$27.00
500g	98%	in stock	$125.00	$87.00

Description

• Catalog Number: AD61933
• Chemical Name: Z-Pro-OH
• CAS Number: 1148-11-4
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.2625
• MDL Number: MFCD00003170
• SMILES: OC(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1

Computed Properties

• Complexity: 312
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 18
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 4
• XLogP3: 1.7

Upstream Synthesis Route

N-Cbz-L-proline, also known as carbobenzyloxy-L-proline, plays a crucial role in chemical synthesis as a valuable building block in organic chemistry. This compound is widely used as a versatile reagent and intermediate in the synthesis of various pharmaceuticals, agrochemicals, and materials.One key application of N-Cbz-L-proline is in the construction of peptide bonds during peptide synthesis. As a proline derivative, N-Cbz-L-proline serves as a protected form of the amino acid proline, providing stability and facilitating selective reactions. By utilizing N-Cbz-L-proline as a starting material, chemists can efficiently introduce proline into peptides with controlled stereochemistry and regioselectivity.Furthermore, N-Cbz-L-proline is employed in the preparation of proline-containing drugs and bioactive molecules due to its ability to influence the conformation and biological activity of the resulting compounds. Its presence in the molecular structure can enhance the binding affinity, metabolic stability, and pharmacokinetic properties of the target molecules, making it a valuable tool in drug discovery and development.In addition to peptide synthesis, N-Cbz-L-proline finds application in asymmetric catalysis, where it serves as a chiral ligand or organocatalyst for various transformations such as aldol reactions, Michael additions, and Mannich reactions. The unique structural features of N-Cbz-L-proline enable the formation of complex molecules with high chemo-, regio-, and enantioselectivity, making it a valuable asset in the synthesis of optically active compounds.Overall, the versatility and utility of N-Cbz-L-proline make it an indispensable component in the toolbox of synthetic chemists for the efficient and selective construction of diverse chemical structures with pharmaceutical, agricultural, and material applications.

Literature

• Prolidase-dependent regulation of TGF β (corrected) and TGF β receptor expressions in human skin fibroblasts.

  European journal of pharmacology 20101215

• Activity of prolidase isoenzymes in the rat brain: subcellular and regional distribution during development.

  Brain research 20091215

• Alpha-ketoglutarate stimulates procollagen production in cultured human dermal fibroblasts, and decreases UVB-induced wrinkle formation following topical application on the dorsal skin of hairless mice.

  Biological & pharmaceutical bulletin 20070801

• Proline prodrug of melphalan targeted to prolidase, a prodrug activating enzyme overexpressed in melanoma.

  Pharmaceutical research 20070701

• Prolidase isoenzymes in the rat: their organ distribution, developmental change and specific inhibitors.

  Pediatric research 20070701

• N-benzyloxycarbonyl-L-proline: an in vitro and in vivo inhibitor of prolidase.

  Biochimica et biophysica acta 20050630

• Modification of porcine pancreatic lipase with Z-proline.

  Preparative biochemistry & biotechnology 20050101