1269759-74-1

Basic information

• Product Name: N-(2-Boc-aminoethyl)-N-(chloroacetyl)-N-(3-Cbz-amino-L-alanyl)methyl ester
• Synonyms: N-(2-Boc-aminoethyl)-N-(chloroacetyl)-N-(3-Cbz-amino-L-alanyl)methyl ester
• CAS NO: 1269759-74-1
• Molecular Weight: 471.938
• Mol File: 1269759-74-1.mol

Chemical Properties

• CAS DataBase Reference: N-(2-Boc-aminoethyl)-N-(chloroacetyl)-N-(3-Cbz-amino-L-alanyl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Boc-aminoethyl)-N-(chloroacetyl)-N-(3-Cbz-amino-L-alanyl)methyl ester(1269759-74-1)
• EPA Substance Registry System: N-(2-Boc-aminoethyl)-N-(chloroacetyl)-N-(3-Cbz-amino-L-alanyl)methyl ester(1269759-74-1)

Safety Data

• Hazardous Substances Data: 1269759-74-1(Hazardous Substances Data)

Upstream product

• 1269759-72-9 N-(2-Boc-aminoethyl)-N-(3-Cbz-amino-L-alanyl)methyl ester 
• 79-04-9 chloroacetyl chloride 
• 65710-57-8 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)-L-alanine 
• 61040-22-0 N^β-benzyloxycarbonyl-N^α-Boc-(S)-β-aminoalanine methyl ester 

Downstream Products

• 1269759-78-5 N-(2-Boc-aminoethyl)-N-(thymine-1-ylacetyl)-N-(3-Cbz-amino)-L-alanine 
• 1269759-76-3 N-(2-Boc-aminoethyl)-N-(thymine-1-acetyl)-N-(3-Cbz-amino-L-alanyl)methyl ester 

Relevant articles and documents

Aminomethylene peptide nucleic acid (am -PNA): Synthesis, regio-/stereospecific DNA binding, and differential cell uptake of (α/γ, R / S) am- PNA analogues

Inherently chiral, cationic am-PNAs having pendant aminomethylene groups at α(R/S) or γ(S) sites on PNA backbone have been synthesized. The modified PNAs are shown to stabilize duplexes with complementary cDNA in a regio- and stereo-preferred manner with γ(S)-am PNA superior to α(R/S)-am PNAs and α(R)-am PNA better than the α(S) isomer. The enhanced stabilization of am-PNA:DNA duplexes is accompanied by a greater discrimination of mismatched bases. This seems to be a combined result of both electrostatic interactions and conformational preorganization of backbone favoring the cDNA binding. The am-PNAs are demonstrated to effectively traverse the cell membrane, localize in the nucleus of HeLa cells, and exhibit low toxicity to cells.

PNAs grafted with (α/γ, R/S)-aminomethylene pendants: Regio and stereo specific effects on DNA binding and improved cell uptake

PNAs grafted with cationic aminomethylene (am) pendants on the backbone at the glycyl (α) or ethylenediamine (γ) segments show regio (α/γ) and stereochemistry (R/S) dependent binding with complementary DNA. These are efficiently taken up by cells, with γ(S-am) aeg-PNA being the best in all properties.