258332-57-9

Basic information

• Product Name: N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER
• Synonyms: N-[3-(TERT-BUTOXYCARBONYLAMINO)PROPYL]GLYCINE ETHYL ESTER;N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER;N-[3-(tert-Butoxycarbonylamino)propyl]glycine Ethyl Ester;Ethyl 2-((3-((tert-butoxycarbonyl)
• CAS NO: 258332-57-9
• Molecular Formula: C₁₂H₂₄N₂O₄
• Molecular Weight: 260.33
• Mol File: 258332-57-9.mol

Chemical Properties

• Boiling Point: 368.903°C at 760 mmHg
• Flash Point: 176.907°C
• Appearance: /
• Density: 1.036g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4550-1.4590
• Storage Temp.: Refrigerator
• PKA: 12.77±0.46(Predicted)
• CAS DataBase Reference: N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER(258332-57-9)
• EPA Substance Registry System: N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER(258332-57-9)

Safety Data

• Hazardous Substances Data: 258332-57-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER is used as a reagent for the synthesis of complex organic molecules, providing a protected form of glycine that can be selectively modified to achieve desired structural features in the final product.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER is used as a building block for the synthesis of peptide-based drugs. Its protected form allows for the controlled assembly of peptide chains, which is crucial for the development of effective and stable medications.
Used in Peptide Synthesis:
N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER is utilized as a protected amino acid in peptide synthesis, facilitating the stepwise construction of peptide sequences. The BOC group ensures that the amine group remains unreactive until it is specifically deprotected, allowing for precise control over the synthesis process.
Used in Research and Development:
In the field of organic chemistry research, N-[3-(BOC-AMINO)PROPYL]GLYCINE ETHYL ESTER is used as a versatile compound for exploring new synthetic pathways and developing innovative methods for the preparation of complex organic molecules. Its unique properties make it a valuable tool for advancing scientific understanding and discovering new applications.

InChI:InChI=1/C12H24N2O4/c1-5-17-10(15)9-13-7-6-8-14-11(16)18-12(2,3)4/h13H,5-9H2,1-4H3,(H,14,16)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 75178-96-0 N-Boc-1,3-diaminopropane 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 143192-31-8 N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-(5-((tert-butoxycarbonyl)amino)propyl)glycine 
• 352285-39-3 {3-[tert-butoxycarbonyl-({[(1-methanesulfonyl-1H-indol-2-yl)-m-tolyl-methyl]-carbamoyl}-methyl)-amino]-propyl}-carbamic acid tert-butyl ester 
• 352285-41-7 {3-[({[benzofuran-2-yl-(4-chloro-phenyl)-methyl]-carbamoyl}-methyl)-tert-butoxycarbonyl-amino]-propyl}-carbamic acid tert-butyl ester 
• 352285-28-0 (R)-[2-(3-Amino-propylamino)-acetoxy]-phenyl-acetic acid methyl ester 
• 192124-66-6 N,N'-bis(tert-butoxycarbonyl)-(3-aminopropyl)-glycine 
• 367955-18-8 {N-[3-(tert-Butoxycarbonylamino)propyl]-N-(2,4-difluoro-5-methylbenzoyl)amino}acetic acid ethyl ester 
• 367955-16-6 {N-[3-(tert-Butoxycarbonylamino)propyl]-N-(pentafluorobenzoyl)amino}acetic acid ethyl ester 

Relevant articles and documents

Peptide/peptoid hybrid oligomers: The influence of hydrophobicity and relative side-chain length on antibacterial activity and cell selectivity

Previous optimisation studies of peptide/peptoid hybrids typically comprise comparison of structurally related analogues displaying different oligomer length and diverse side chains. The present work concerns a systematically constructed series of 16 closely related 12-mer oligomers with an alternating cationic/hydrophobic design, representing a wide range of hydrophobicity and differences in relative side-chain lengths. The aim was to explore and rationalise the structure-activity relationships within a subclass of oligomers displaying variation of three structural features: (i) cationic side-chain length, (ii) hydrophobic side-chain length, and (iii) type of residue that is of a flexible peptoid nature. Increased side-chain length of cationic residues led to reduced hydrophobicity till the side chains became more extended than the aromatic/hydrophobic side chains, at which point hydrophobicity increased slightly. Evaluation of antibacterial activity revealed that analogues with lowest hydrophobicity exhibited reduced activity against E. coli, while oligomers with the shortest cationic side chains were most potent against P. aeruginosa. Thus, membrane-disruptive interaction with P. aeruginosa appears to be promoted by a hydrophobic surface of the oligomers (comprised of the aromatic groups shielding the cationic side chains). Peptidomimetics with short cationic side chains exhibit increased hemolytic properties as well as give rise to decreased HepG2 (hepatoblastoma G2 cell line) cell viability. An optimal hydrophobicity window could be defined by a threshold of minimal hydrophobicity conferring activity toward E. coli and a threshold for maximal hydrophobicity, beyond which cell selectivity was lost.

Fluorous Peptide Nucleic Acids: PNA Analogues with Fluorine in Backbone (γ-CF2-apg-PNA) Enhance Cellular Uptake

Fluorous PNA analogues possessing fluorine as inherent part of aminopropylglycine (apg) backbone (γ-CF2-apg PNA) have been synthesized and evaluated for biophysical and cell penetrating properties. These form duplexes of higher thermal stability with cRNA than cDNA, although destabilized compared to duplexes of standard aeg-PNA. Cellular uptake of the fluorinated γ-CF2-apg PNAs in NIH 3T3 and HeLa cells was 2-3-fold higher compared to that of nonfluorinated apg PNA, with NIH 3T3 cells showing better permeability compared to HeLa cells. The backbone fluorinated PNAs, which are first in this class, when combined with other chemical modifications may have potential for future PNA-based antisense agents.

Synthesis of nonpolar peptide nucleic acid monomers containing fluoroaromatics

A general strategy for the synthesis of nonpolar peptide nucleic acid monomers containing fluoroaromatics (F-PNA) is described. These compounds have been designed as hybrid analogues of the difluorotoluene nucleoside, F (1) with PNA. Fluorophenylacetic ac

Chiral recognition by CD-sensitive dimeric zinc porphyrin host. 1. Chiroptical protocol for absolute configurational assignments of monoalcohols and primary monoamines

A general microscale protocol for the determination of absolute configurations of primary amino groups or secondary hydroxyl groups linked to a single stereogenic center is described. The chiral substrates are linked to the achiral trifunctional bidentate carrier molecule (3-aminopropylamino)acetic acid (1, H2NCH2CH2CH2NHCH2COOH) and the resultant conjugates are then complexed with dimeric zinc porphyrin host 2 giving rise to 1:1 host/guest sandwiched complexes. These complexes exhibit exciton-coupled bisignate CD spectra due to stereodifferentiation leading to preferred porphyrin helicity. Since the chiral sense of twist between the two porphyrins in the complex is dictated by the stereogenic center of the substrate, the sign of the couplet determines the absolute configuration at this center. The twist of the porphyrin tweezer in the complex can be predicted from the relative steric sizes of the groups flanking the stereogenic center, such that the bulkier group protrudes from the complex sandwich. In certain α-hydroxy esters and α-amino esters, electronic factors and hydrogen bonding govern the preferred conformation of the complex, and hence the CD spectra.