475591-59-4

Basic information

• Product Name: Boc-NH-PEG2-NH-Boc
• Synonyms: Boc-NH-PEG2-NH-Boc
• CAS NO: 475591-59-4
• Molecular Formula: C16H32N2O6
• Molecular Weight: 348.43508
• Mol File: 475591-59-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Boc-NH-PEG2-NH-Boc(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-NH-PEG2-NH-Boc(475591-59-4)
• EPA Substance Registry System: Boc-NH-PEG2-NH-Boc(475591-59-4)

Safety Data

• Hazardous Substances Data: 475591-59-4(Hazardous Substances Data)

Usage

Description

Boc-NH-PEG2-NH-Boc is a synthetic compound that features two Boc (tert-butyloxycarbonyl) protecting groups and a hydrophilic polyethylene glycol (PEG) spacer with a molecular weight of approximately 2 kDa. The Boc groups are acid labile, which means they can be removed under acidic conditions, while the PEG linker enhances the compound's solubility in aqueous environments.

Uses

Used in Pharmaceutical Industry:
Boc-NH-PEG2-NH-Boc is used as a protecting group for peptide synthesis to facilitate the process and improve the yield of the desired peptide product. The acid lability of the Boc groups allows for selective deprotection under controlled conditions, enabling the stepwise assembly of complex peptide sequences.
Used in Drug Delivery Systems:
In the field of drug delivery, Boc-NH-PEG2-NH-Boc is utilized as a component in the design of prodrugs or drug conjugates. The hydrophilic PEG spacer can improve the solubility and bioavailability of hydrophobic drugs, while the Boc protecting groups can be used to mask the reactivity of functional groups until the drug reaches its target site, where the Boc groups can be removed by cellular enzymes or acidic conditions.
Used in Bioconjugation and Chemical Synthesis:
Boc-NH-PEG2-NH-Boc serves as a versatile linker in bioconjugation chemistry, allowing for the attachment of various biologically active molecules, such as peptides, proteins, or small molecules, to a PEG backbone. This can enhance the stability, solubility, and circulation time of these molecules in biological systems, while the Boc protecting groups provide a means to control the reactivity and timing of the conjugation process.
Used in Materials Science:
In materials science, Boc-NH-PEG2-NH-Boc can be employed as a building block for the development of novel polymeric materials with tailored properties. The hydrophilic PEG spacer can improve the compatibility of the polymer with aqueous environments, while the Boc protecting groups can be used to control the polymerization process or to introduce functional groups at specific locations within the polymer structure.

Upstream product

• 929-59-9 3,6-dioxa-1,8-diaminooctane 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Flow-mediated synthesis of Boc, Fmoc, and Dd iv monoprotected diamines

A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access to N-Boc-, N-Fmoc-, and N-Ddiv-protected compounds with productivity indexes of 1.2-3.6 g/h.

Evaluation of the synthesis of sialic Acid-PAMAM glycodendrimers without the use of sugar protecting Groups, and the Anti-HIV-1 properties of these compounds

A study was undertaken to evaluate the feasibility of synthesizing six sialic acid-PAMAM glycodendrimers using unprotected sialic acid in as few as 1-4 steps using two different reaction pathways, and to assess the sulfated derivatives for anti-HIV activity. The syntheses were accomplished through either the direct attachment of the sialic acid carboxyl group to amine-terminated PAMAM (a divergent-like approach) using BOP coupling, or by first reacting sialic acid with a polar bifunctional spacer molecule, attaching the sugar-linker to carboxy-terminated PAMAM (a convergent-like approach), and again using BOP-mediated coupling reactions. It was hypothesized that the latter approach would be the most successful method, as any steric congestion between the sialic acid and the PAMAM would be minimized using an intervening polar linker. However, the divergent-like synthesis proved to be the superior method, resulting in 11.4%, 14%, and 28% of the fully substituted generations 0, 1, and 2 sialic acid-PAMAM conjugates, respectively, as compared to 6.4% of only the generation ?0.5 sialic acid-linker-PAMAM conjugate for the convergent-like method. Upon sulfation of the four glycodendrimers, binding capabilities to the recombinant HIV protein, gp120, were assessed using an ELISA assay. Compounds that showed promising binding characteristics were then further assessed for inhibition of HIV-1 infection using a well-characterized luciferase reporter gene neutralization assay. The generation 2 sulfated sialic acid-PAMAM glycodendrimer, sulfo-6, bearing 16 sialic acids with 11 sulfate groups incorporated at 4.03% sulfur content by weight, was found to inhibit all four HIV-1 strains tested in the low micromolar range.

Lipophilic peptide nucleic acids containing a 1,3-diyne function: Synthesis, characterization and production of derived polydiacetylene liposomes

Adenine-, cytosine- and thymine-containing peptide nucleic acid (PNA) monomers have been synthesized in which either diacetylenic or stearoyl moieties are attached to the N-or C-terminus; the diacetylenic group is embedded within a long hydrocarbon chain.