14030-00-3

Basic information

• Product Name: Z-PRO-ALA-OH
• Synonyms: N-CARBOBENZOXY-L-PROPYL-L-ALANINE;Z-PRO-ALA-OH;Z-L-PROLYL-L-ALANINE;N-cbz-pro-ala;N-benzyloxycarbonyl-L-prolyl-L-alanine;N-carbobenzyloxy-Pro-Ala;1-[(Phenylmethoxy)carbonyl]-L-Pro-L-Ala-OH;Cbz-L-Pro-L-Ala-OH
• CAS NO: 14030-00-3
• Molecular Formula: C₁₆H₂₀N₂O₅
• Molecular Weight: 320.34
• EINECS: 237-868-7
• Product Categories: Amino Acid Derivatives
• Mol File: 14030-00-3.mol

Chemical Properties

• Melting Point: 161-162 °C(Solv: water (7732-18-5))
• Boiling Point: 582.3 °C at 760 mmHg
• Flash Point: 306 °C
• Appearance: /
• Density: 1.301 g/cm³
• Vapor Pressure: 2.11E-14mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: -15°C
• PKA: 3.70±0.10(Predicted)
• CAS DataBase Reference: Z-PRO-ALA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PRO-ALA-OH(14030-00-3)
• EPA Substance Registry System: Z-PRO-ALA-OH(14030-00-3)

Safety Data

• Hazardous Substances Data: 14030-00-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Z-PRO-ALA-OH is used as a synthetic peptide in pharmaceutical research for its ability to mimic the structure and function of natural peptides, aiding in the development of new drugs and therapies.
Used in Anti-Inflammatory Applications:
Z-PRO-ALA-OH is used as an anti-inflammatory agent, potentially reducing inflammation and promoting healing in various medical conditions.
Used in Anti-Oxidant Applications:
Z-PRO-ALA-OH is used as an anti-oxidant, helping to neutralize harmful free radicals and protect cells from oxidative damage.
Used in Skin Regeneration and Wound Healing:
Z-PRO-ALA-OH is used as a component in skin regeneration and wound healing treatments, due to its unique amino acid composition that promotes tissue repair and recovery.
Used in Peptide Synthesis for Drug Development:
Z-PRO-ALA-OH is used as a building block in the synthesis of larger peptide compounds, contributing to the development of new drugs and medical applications.

InChI:InChI=1/C16H20N2O5/c1-11(15(20)21)17-14(19)13-8-5-9-18(13)16(22)23-10-12-6-3-2-4-7-12/h2-4,6-7,11,13H,5,8-10H2,1H3,(H,17,19)(H,20,21)

Upstream product

• 51782-87-7 Cbz-L-proline-L-alanine methyl ester 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 886981-23-3 benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)tetrahydro-1H-pyrrole-1-carboxylate 
• 56-41-7 L-alanin 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 

Downstream Products

• 34079-31-7 Z-Pro-NH₂ 
• 6422-36-2 L-prolyl-L-alanine 
• 6422-36-2 N-L-prolyl-L-alanine 

Relevant articles and documents

Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins

The development of unnatural tripeptides as highly enantioselective organocatalysts for the asymmetric aldol reaction of isatins was achieved. H-Pro-Gly-D-Ala-OH with the D-alanine residue as the C-terminal amino acid residue expressed the best enantioselectivity. The H-Pro-Gly-D-Ala-OH-catalyzed reaction of isatins gave various aldol adducts with up to 93% yield and up to 97% ee. Investigation of the transition state via DFT calculation revealed that high optical purity was realized by the D-alanine controlled steric environment.

Organocatalyzed Asymmetric Aldol Reaction of α-Keto Amides with A Tripeptide Catalyst

An organocatalyzed asymmetric aldol reaction of α-keto amides was developed. An N-terminal 4- trans -siloxyproline-based tripeptide with an l - tert -leucine unit adjacent to the 4- trans -siloxyproline residue was used to catalyze the reaction between various α-keto amides and acetone, to produce the corresponding aldol adducts with up to 99% yield and 91% ee.

Efficient peptide coupling involving sterically hindered amino acids

(Chemical Equation Presented) Hindered amino acids have been introduced into peptide chains by coupling N-(Cbz- and Fmoc-α-aminoacyl) benzotriazoles with amino acids, wherein at least one of the components was sterically hindered, to provide compounds 3a-e, (3c +3 c′), 5a-d, (5a + 5a′), 6a-c, (6b + 6b′), 8a-c, 9a-e, 10a-d, and (10a + 10a′) in isolated yields of 41-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. The benzotriazole activation methodology is a new route for the synthesis of sterically hindered peptides. (Note: compound numbers written within brackets represent diastereomeric mixtures or racemates; compound numbers without brackets represent enantiomers.)