16652-71-4

Basic information

• Product Name: L-Proline benzyl ester hydrochloride
• Synonyms: L-PYRROLIDINE-2-CARBOXYLIC ACID BENZYL ESTER HCL;L-PROLINE BENZYL ESTER;L-PROLINE BENZYL ESTER HCL;L-PROLINE BENZYL ESTER HYDROCHLORIDE SALT;L-PROLINE BENZYL ESTER MONOHYDROCHLORIDE;H-PRO-OBZL;H-PRO-OBZL HCL;PROLINE-OBZL HCL
• CAS NO: 16652-71-4
• Molecular Formula: C₁₂H₁₆NO₂*Cl
• Molecular Weight: 241.71
• EINECS: 240-700-5
• Product Categories: Amino Acid Derivatives;Amino Acids;Proline [Pro, P];Amino Acids and Derivatives;Amino Acid Benzyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Peptide Synthesis;Proline
• Mol File: 16652-71-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 148-151 °C(lit.)
• Boiling Point: 309 °C at 760 mmHg
• Flash Point: 140.7 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.121g/cm3
• Vapor Pressure: 0.000659mmHg at 25°C
• Refractive Index: 1.4365
• Storage Temp.: Store at RT.
• Solubility: soluble in Methanol
• Water Solubility: miscible
• Sensitive: Hygroscopic
• BRN: 3598081
• CAS DataBase Reference: L-Proline benzyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline benzyl ester hydrochloride(16652-71-4)
• EPA Substance Registry System: L-Proline benzyl ester hydrochloride(16652-71-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-22
• Safety Statements: 22-24/25-37/39-26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 16652-71-4(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

L-Proline Benzyl Ester Hydrochloride acts as a reagent in the synthesis and bioactivity of a goralatide analog with anti-leukemic activity.

InChI:InChI=1/C12H15NO2/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10/h1-3,5-6,11,13H,4,7-9H2/p+1/t11-/m0/s1

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 100-51-6 benzyl alcohol 
• 37787-77-2 Boc-L-proline benzyl ester 
• 147-85-3 L-proline 

Downstream Products

• 29776-70-3 N-(tert-butyloxycarbonyl)-prolyl-proline benzyl ester 
• 58872-03-0 1--L-valyl>-L-proline phenylmethyl ester 
• 83610-44-0 benzyl (2S)-1-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanoyl]pyrrolidine-2-carboxylate 
• 120791-81-3 N-(ethyloxycarbonyl)-(L)-proline benzyl ester 
• 35084-69-6 N-t-butyloxycarbonyl-L-alanyl-L-proline benzyl ester 
• 41036-21-9 (S)-benzyl 1-((R)-2-(tert-butoxycarbonylamino)propanoyl)pyrrolidine-2-carboxylate 
• 70462-58-7 benzyl (tert-butoxycarbonyl)-L-phenylalanyl-L-prolinate 
• 5497-75-6 Z-Arg(NO₂)-Pro-OBzl 
• 245115-69-9 Fmoc-Ala-Pro-OBn 
• 35959-86-5 1-(N,S-ditrityl-L-cysteinyl)-L-proline 
• 54046-53-6 Boc-Arg(NO₂)-Pro-OBzl 
• 786693-03-6 (2S)-1-(4-diazo-4-ethoxycarbonyl-3-oxo-butyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 23361-28-6 N-(tert-butyloxycarbonyl)-L-valyl-L-proline 
• 642090-91-3 (S)-1-[(S)-2-((S)-2-amino-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid benzylamide 

Relevant articles and documents

Synthesis and bioactivity of a Goralatide analog with antileukemic activity

Natural tetrapeptide Goralatide (AcSDKP) is a selective inhibitor of primitive haematopoietic cell proliferation. It is not stable in vivo and decomposes within 4.5 min when applied to live cells. In this work we developed an analog of Goralatide that exhibits cytotoxicity towards human myeloid HL-60, HEL, Nalm-6 leukemia cells, endothelial HUVEC, glioblastoma U251 and transformed kidney 293T cells. The Goralatide analog showed significant stability in organic solution with no tendency to degrade oxidatively.

Synthesis and evaluation of in Vivo anti-hypothermic effect of the N- And C-terminus modified thyrotropin-releasing hormone mimetic: [(4S,5S)-(5-methyl-2-oxooxazolidine-4-yl)-carbonyl]-[3-(thiazol-4-yl)-L-alanyl]-L-prolinamide

We explored orally effective thyrotropin-releasing hormone (TRH) mimetics, which show high central nervous system effects in structure–activity relationship studies based on in vivo antagonistic activity on reserpine-induced hypothermia (anti-hypothermic effect) in mice starting from TRH. This led us to the TRH mimetic: [(4S,5S)-(5-methyl-2-oxooxazolidine-4-yl)carbonyl]-[3-(thiazol-4-yl)-L-alanyl]-L-prolinamide 1, which shows a higher anti-hypothermic effect compared with that of TRH after oral administration. We next attempted further chemical modification of the N- and C-terminus of 1 to find more orally effective TRH mimetics. As a result, we obtained several N- and C-terminus modified TRH mimetics which showed high anti-hypothermic effects.

Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions

Biaryl-bridged cyclic peptides comprise an intriguing class of structurally diverse natural products with significant biological activity. Especially noteworthy are the antibiotics arylomycin and its synthetic analogue G0775, which exhibits potent activity against Gram-negative bacteria. Herein, we present a simple, flexible, and reliable strategy based on activating-group-assisted catalytic oxidative coupling for assembling biaryl-bridged cyclic peptides from natural amino acids. The synthetic approach was utilized for preparing a number of natural and unnatural biaryl-bridged cyclic peptides, including arylomycin/G0775 and RP 66453 cyclic cores.