21285-27-8

Basic information

• Product Name: Z-PRO-VAL-OH
• Synonyms: Z-PRO-VAL-OH;N-[1-[(benzyloxy)carbonyl]-L-prolyl]-L-valine;N-[1-[(Phenylmethoxy)carbonyl]-L-prolyl]-L-valine;Z-L-Pro-L-Val-OH
• CAS NO: 21285-27-8
• Molecular Formula: C₁₈H₂₄N₂O₅
• Molecular Weight: 348.39
• EINECS: 244-312-7
• Mol File: 21285-27-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 587°Cat760mmHg
• Flash Point: 308.8°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 1.27E-14mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: Z-PRO-VAL-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PRO-VAL-OH(21285-27-8)
• EPA Substance Registry System: Z-PRO-VAL-OH(21285-27-8)

Safety Data

• Hazardous Substances Data: 21285-27-8(Hazardous Substances Data)

Usage

General Description

Z-PRO-VAL-OH is a chemical compound that belongs to the family of amino acids, specifically a derivative of proline. It is classified as a non-proteinogenic amino acid, meaning it is not commonly found in proteins but has various biological roles. Z-PRO-VAL-OH is known for its ability to act as a building block for peptides and proteins, playing a crucial role in protein synthesis and structural stability. Additionally, this compound has been studied for its potential therapeutic applications, such as its anti-inflammatory properties and ability to regulate immune responses. Overall, Z-PRO-VAL-OH is a versatile and important molecule with promising biomedical uses.

InChI:InChI=1/C18H24N2O5/c1-12(2)15(17(22)23)19-16(21)14-9-6-10-20(14)18(24)25-11-13-7-4-3-5-8-13/h3-5,7-8,12,14-15H,6,9-11H2,1-2H3,(H,19,21)(H,22,23)

Upstream product

• 72-18-4 L-valine 
• 1280225-77-5 C₂₃H₂₈N₂O₆ 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 4070-48-8 L-Valine methyl ester 
• 6306-52-1 L-valine methylester hydrochloride 
• 13211-31-9 tert-butyl L-valinate 
• 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 
• 99909-22-5 Z-Pro-Val-OBzl 
• 26061-29-0 (S)-benzyl 2-((S)-1-tert-butoxy-3-methyl-1-oxobutan-2-ylcarbamoyl)pyrrolidine-1-carboxylate 
• 2874-20-6 benzyloxycarbonyl-L-prolin-L-valin methyl ester 

Downstream Products

• 52899-09-9 N-L-prolyl-L-valine 
• 67545-92-0 (S)-2-((S)-4-isopropyl-5-oxo-4,5-dihydro-oxazol-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 52899-09-9 (S)-prolyl-(S)-valine 
• 121075-28-3 N⁶-benzyloxycarbonyl-N²-[N-(1-benzyloxycarbonyl-L-prolyl)-L-valyl]-L-lysine 
• 126134-64-3 Z-Leu-Ile-Pro-Val-Pro-OPFP 
• 126134-63-2 Z-Leu-Ile-Pro-Val-Pro-OCH₃ 
• 126134-62-1 Z-Ile-Pro-Val-Pro-OCH₃ 
• 99909-25-8 Z-Pro-Val-Leu-Gly-Pro-Val-O-Bzl 
• 99909-24-7 Z-Pro-Val-Leu-Gly-OH 
• 100690-01-5 Z-L-Pro-L-Val-L-Phe-Cm(O-t-Bu)-L-Val-OEt 
• 99909-23-6 Z-Pro-Val-Leu-Gly-OBzl 
• 73871-01-9 Z-L-Pro-L-Val-δ-Z-L-Orn-OMe 
• 28334-65-8 Z-S-Pro-S-Val-S-Pro-OtBu 
• 51782-86-6 Z-Pro-Val-Pro-OCH₃ 

Relevant articles and documents

Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated α-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4- dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-l-Orn(Boc)-Val-OMe, Fmoc-l-Cys(trt)-Gly-OEt and Boc-l-Tyr-Gly-OEt is presented.

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.)

ARYLOXY AND ARYLACYLOXY METHYL KETONES AS THIOL PROTEASE INHIBITORS

Thiol protease inhibitors are disclosed having the formula: STR1 or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein:n is 0 or 1;m is 0, 1 or 2;X is H or an N-protecting group; each Y is independently an optionally protected α-amino acid residue;R is an optionally protected α-amino acid side chain that is H or CH 3 or that is bonded to the α-carbon atom to which it is attached by a methylene, methine or phenyl radical; andR' is optionally substituted aryl.