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
• Article Data: 3

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

General Description

Z-PRO-ALA-OH is a chemical compound consisting of three amino acids - proline, alanine, and hydroxyproline, linked together in a specific sequence. It is a synthetic peptide often used in biological and pharmaceutical research for its ability to mimic the structure and function of natural peptides. Z-PRO-ALA-OH is known for its potential therapeutic effects, such as anti-inflammatory and anti-oxidant properties. It is also used as a building block in the synthesis of larger peptide compounds for drug development and medical applications. Additionally, Z-PRO-ALA-OH has been studied for its potential role in promoting skin regeneration and wound healing due to its unique amino acid composition.

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.

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.)