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

Description

L-Proline benzyl ester hydrochloride is a white powder chemical compound that serves as a reagent in the synthesis and bioactivity of various compounds, including goralatide analogs with anti-leukemic activity.

Uses

Used in Pharmaceutical Industry:
L-Proline benzyl ester hydrochloride is used as a reagent for the synthesis of goralatide analogs, which possess anti-leukemic properties. This application aids in the development of potential treatments for leukemia and other related blood disorders.

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

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

Downstream Products

• 79190-57-1 1-[N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosyl]-L-proline-benzyl ester 
• 87297-08-3 1-methoxycarbonylmethyl-L-proline-benzyl ester 
• 88105-65-1 (S)-1-phenylacetyl-pyrrolidine-2-carboxylic acid benzyl ester 
• 29776-78-1 (S)-1-(2-tert-butoxycarbonylaminoacetyl)pyrrolidine-2-carboxylic acid benzyl ester 
• 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 
• 126255-75-2 N-(E)-crotonyl-(S)-prolinbenzylester 
• 126255-78-5 N,N'-Fumaroylbis((S)-prolin-benzylester) 
• 41591-34-8 Ac-Ala-Pro-OBn 
• 120791-81-3 N-(ethyloxycarbonyl)-(L)-proline benzyl ester 
• 35084-69-6 N-t-butyloxycarbonyl-L-alanyl-L-proline benzyl ester 
• 92010-16-7 (S)-benzyl 1-(3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate 
• 68280-74-0 benzyl N⁶-((benzyloxy)carbonyl)-N²-(tert-butoxycarbonyl)-L-lysyl-L-prolinate 

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.

Design, synthesis and biological evaluation of new bivalent quinazoline analogues as IAP antagonists

We recently reported the biological evaluations of monovalent IAP antagonist 7 with good potency (MDA-MB-231, IC50 = 19 nM). In an effort to increase cellular activity and improve favorable drug-like properties, we newly designed and synthesized bivalent analogues based on quinazoline structure of 7. Optimization of cellular potency and CYP inhibition led to the identification of 27, which showed dramatic increase of over 100-fold (IC50 = 0.14 nM) and caused substantial tumor regressions in MDA-MB-231 xenograft model. These results strongly support 27 as a promising bivalent antagonist for the development of an effective anti-tumor approaches.

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.