139166-80-6

Basic information

• Product Name: BOC-PNA-T-OH
• Synonyms: BOC-PNA-T-OH;N-[2-(BOC-AMINO)ETHYL]-N-(THYMIN-1-YLACETYL)GLYCINE;(BOC-T-AEG-OH)
• CAS NO: 139166-80-6
• Molecular Formula: C₁₆H₂₄N₄O₇
• Molecular Weight: 384.38
• Mol File: 139166-80-6.mol

Chemical Properties

• Appearance: /
• Density: 1.301±0.06 g/cm3(Predicted)
• PKA: 3.33±0.10(Predicted)
• CAS DataBase Reference: BOC-PNA-T-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-PNA-T-OH(139166-80-6)
• EPA Substance Registry System: BOC-PNA-T-OH(139166-80-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 139166-80-6(Hazardous Substances Data)

Usage

Uses

Used in Molecular Biology:
BOC-PNA-T-OH is used as a monomer in the synthesis of PNA oligomers for applications in molecular biology. Its role is crucial in the development of PNA probes that can hybridize with DNA or RNA, offering advantages such as increased stability and specificity.
Used in Diagnostics:
In the diagnostics industry, BOC-PNA-T-OH is used as a component in the creation of PNA-based detection tools. These tools leverage the high binding affinity of PNA to DNA or RNA for accurate and reliable diagnostic assays.
Used in Therapeutics:
BOC-PNA-T-OH is utilized as a building block for PNA conjugates that have potential therapeutic applications. These conjugates can be designed to target specific nucleic acid sequences, offering a new avenue for the development of targeted therapies.
Used in Drug Development:
In the field of drug development, BOC-PNA-T-OH is used as a starting material for the synthesis of PNA-based drugs. These drugs can be designed to modulate gene expression or disrupt specific nucleic acid interactions, providing new therapeutic strategies for various diseases.
Used in Peptide Nucleic Acid Research:
BOC-PNA-T-OH is extensively used in research related to peptide nucleic acids. It serves as a fundamental component in the exploration of PNA properties, mechanisms of action, and potential applications in various fields, including biotechnology and medicine.

Upstream product

• 57260-73-8 N-BOC-1,2-diaminoethane 
• 20924-05-4 thymidyl acetic acid 
• 134456-94-3 methyl (5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)ethanoate 
• 90495-99-1 N-(2-tert-butoxycarbonylaminoethyl)aminoacetic acid 
• 149411-93-8 N-(2-t-butoxycarbonylaminoethyl)-N-(thymin-1-ylacetyl)glycine ethyl ester 
• 65-71-4 thymin 
• 139166-79-3 1-thyminylacetic acid pentafluorophenyl ester 
• 128421-86-3 methyl N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate 
• 72648-80-7 ethyl 2-[2-(tert-butoxycarbonylamino)ethyl-[3-[[4-(4,5-difluoro-2-methylsulfanyl-phenyl)phenoxy]methyl]benzoyl]amino]acetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 152774-08-8 methyl N-[2-(Boc-amino)ethyl]-N-(thymin-1-ylacethyl) glycinate 

Downstream Products

• 1092571-18-0 C₄₀H₅₈N₂₂O₁₅ 
• 1092571-16-8 C₄₁H₆₀N₂₂O₁₅ 
• 289684-56-6 N-[9-(2-{7-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-3,9-dioxo-1,4,7,10tetraaza-cyclododec-1-yl}-2-oxo-ethyl)-9H-purin-6-yl]-benzamide 
• 289684-54-4 7-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-3,9-dioxo-1,4,7,10tetraaza-cyclododecane-1-carboxylic acid benzyl ester 
• 1026796-74-6 {[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-amino}-acetic acid 
• 345201-79-8 3-{[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-propionic acid 
• 345201-81-2 2-{[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-propionic acid 
• 345201-80-1 2-{[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-propionic acid 
• 345201-78-7 {[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid 
• 681430-78-4 3-{[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-phenyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-propionic acid methyl ester 
• 345201-73-2 {[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid methyl ester 
• 169396-92-3 2-(N-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid 
• 289684-71-5 {benzyloxycarbonyl-[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-ethyl]-amino}-acetic acid methyl ester 
• 139166-81-7 {(2-tert-Butoxycarbonylamino-ethyl)-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid pentafluorophenyl ester 

Relevant articles and documents

Synthesis and polymerisation of lipophilic peptide nucleic acids derived from stearic acid and pentacosa-10,12-diynoic acid

The adenine, cytosine and thymine peptide nucleic acid (PNA) monomers and PNA T10 oligomers bearing either a diacetylenic or stearoyl moiety at the N- or C-terminus have been successfully prepared. The resulting thymine monomeric and T10/

A convenient and scalable synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride. Key intermediates for peptide nucleic acid synthesis

An improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt is reported. The synthesis is based on the reductive alkylation of Bocethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatography. This compound is suitable, as is, for the synthesis peptide nucleic acid monomers. Further, conversion to the hydrochloride salt provides a stable, nonhygroscopic solid that is a convenient form for handling and storage.

Pharmaceuticals for enhanced delivery to disease targets

Pharmaceuticals for enhanced delivery to a disease target comprises a pair of compounds. The first compound comprises a first oligopeptide conjugated to a first moiety for coupling with a diagnostic or therapeutic active agent. The second compound comprises a second oligopeptide conjugated to a targeting species having a targeting moiety capable of binding to a target. The second oligopeptide has a sequence that is complementary to a sequence of the first oligopeptide. The first and second oligopeptides can be complementary PNA sequences. The pharmaceuticals are administered into a subject in methods for diagnosing or treating a disease condition, or assessing the effectiveness of a treatment of the disease condition.

CONVENIENT AND SCALABLE SYNTHESIS OF ETHYL N-[(2-BOC-AMINO) ETHYL] GLYCINATE AND ITS HYDROCHLORIDE SALT

The present invention discloses an improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt. The synthesis is based on the reductive alkylation of Boc-ethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatography. This compound is suitable, as is, for the synthesis peptide nucleic acid monomers. Further, conversion to the hydrochloride salt provides a stable, non-hygroscopic solid that is a convenient form for handling and storage.

PEPTIDE NUCLEIC ACID CONJUGATES

A novel class of peptide nucleic acids are described which include a conjugate attached thereto. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

Backbone modifications of aromatic peptide nucleic acid (APNA) monomers and their hybridization properties with DNA and RNA

Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-β-alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in triplex formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.

Multicomponent synthesis of novel amino acid-nucleobase chimeras: aA versatile approach to PNA-monomers

This paper describes a multicomponent approach to novel totally protected precursors of PNA-monomers via Ugi 4CC. The obtained bisamides are converted into several partially protected PNA-monomers or derivatives thereof using three different procedures. Methods for hydrolysis are shown to be dependent on the nature of the isocyano component required for Ugi 4CC. Several novel monomers suitable for oligomer synthesis are prepared demonstrating the high versatility of the reaction sequence. Copyright (C) 2000 Elsevier Science Ltd.

Synthesis and photochemical behavior of peptide nucleic acid dimers and analogues containing 4-thiothymine: Unprecedented (5-4) photoadduct reversion

Pna dimers 1, 5, containing either 4-thiothymine or N3-methyl- 4-thiothymine, were prepared, and the crystal structure of compound 3 was established. With regard to their photochemistry none of these PNA analogues were able to fully mimic the p

Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization

The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described.The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared v