139428-96-9

Basic information

• Product Name: BOC-CYS(BZL)-OL
• Synonyms: N-ALPHA-T-BOC-S-BENZYL-L-CYSTEINOL;N-T-BUTOXYCARBONYL-S-BENZYL-L-CYSTEINOL;BOC-(R)-2-AMINO-3-BENZYLTHIO-1-PROPANOL;BOC-S-BENZYL-L-CYSTEINOL;BOC-CYS(BZL)-OL;BOC-CYSTEINOL(BZL);Boc-L-Cys(Bzl)-ol;N-alpha-t-Butyloxycarbonyl-S-benzyl-L-cysteinol, (R)-2-(t-Butyloxycarbonyl-amino)-3-benzylthio-1-propanol
• CAS NO: 139428-96-9
• Molecular Formula: C₁₅H₂₃NO₃S
• Molecular Weight: 297.41
• Product Categories: Amino Acids;Amino Alcohols;Boc-Amino acid series
• Mol File: 139428-96-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 56-58 °C
• Boiling Point: 442.914 °C at 760 mmHg
• Flash Point: 221.667 °C
• Appearance: /
• Density: 1.135 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: Store at 0°C
• PKA: 11.72±0.46(Predicted)
• CAS DataBase Reference: BOC-CYS(BZL)-OL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-CYS(BZL)-OL(139428-96-9)
• EPA Substance Registry System: BOC-CYS(BZL)-OL(139428-96-9)

Safety Data

• Hazardous Substances Data: 139428-96-9(Hazardous Substances Data)

Usage

General Description

BOC-CYS(BZL)-OL, also known as Boc-protected cysteine with benzyl ester group, is a chemical compound commonly used in peptide synthesis and bioconjugation. The BOC group serves as a protecting group to the cysteine amino acid, ensuring its stability during the synthesis process. The benzyl ester group provides a convenient handle for further chemical modification and bioconjugation. BOC-CYS(BZL)-OL is an important building block in the creation of peptide and protein-based pharmaceuticals and research reagents. Its versatile nature and stability make it a valuable tool in the field of molecular biology and drug development.

InChI:InChI=1/C15H23NO3S/c1-15(2,3)19-14(18)16-13(9-17)11-20-10-12-7-5-4-6-8-12/h4-8,13,17H,9-11H2,1-3H3,(H,16,18)/t13-/m1/s1

Upstream product

• 22728-88-7 S-benzylcysteine methyl ester 
• 3054-01-1 S-benzyl-L-cysteine 
• 5068-28-0 (2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid 
• 55478-08-5 N-[(1,1-dimethylethoxy)-carbonyl]-S-(phenylmethyl)-L-cysteine methyl Ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 85803-43-6 (1S)-1-(benzylthiomethyl)-2-hydroxyethylamine 

Downstream Products

• 1069127-51-0 N-tert-butoxycarbonyl-2-azido-1-(benzylthiomethyl)ethylamine 
• 139429-21-3 (S)-1-((S)-2-Amino-3-benzylsulfanyl-propyldisulfanylmethyl)-2-benzylsulfanyl-ethylamine; compound with trifluoro-acetic acid 
• 135950-01-5 ((R)-2-Benzylsulfanyl-1-mercaptomethyl-ethyl)-carbamic acid tert-butyl ester 
• 879219-18-8 [1-benzylsulfanylmethyl-2-(5-fluoro-2,3-dihydro-indol-1-yl)-ethyl]-carbamic acid tert-butyl ester 
• 273401-71-1 (1-benzyloxymethyl-2-benzylsulfanyl-ethyl)-carbamic acid tert-butyl ester 
• 118546-67-1 (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)aminopropionaldehyde 
• 139429-03-1 Thioacetic acid S-((S)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propyl) ester 

Relevant articles and documents

Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution

Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine. These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission in the UV-A (~380 nm) with a relatively large Stokes shift (5700 cm?1). No significant solvatochromism was observed in both ground and excited states. Unexpectedly, the benzoxazole derivatives presented much higher fluorescence quantum yield values (40–80%) of compared to the sulfur analogues (3–6%). In addition, the DNA binding assays indicated that these compounds presented strong interaction with CT-DNA, which could be attributed to π-stacking and intermolecular hydrogen-bonding. The interaction of the benzazoles with bovine serum albumin (BSA) was also investigated, where a suppression mechanism was observed. In each case, docking was performed to better understand the observed interactions.

Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: Optimization of P1 and N-aryl

A systematic study of anilines led to the discovery of a metabolically robust fluoroindoline replacement for the alkoxy aniline toxicophore in 1. Investigations of the P1 pocket resulted in the discovery of a wide tolerance of functionality leading to the discovery of 11 as a potent and selective inhibitor of cathepsin S.

One-pot synthesis of N-protected β-chiral amino alcohols

N-tert-butyloxycarbonyl-S-benzyl-cysteine, N-fluorenylmethyloxycarbonyl-alanine-, S-trityl-cysteine-, O-tert-butyl-serine- and O-tertbutyl-tyrosine were converted to the corresponding alcohols via sodium borohydride reduction of their in situ formed methy