47461-65-4

Basic information

• Product Name: 4-Cbz-amino-2-Boc-amino-butyric acid
• Synonyms: 4-Cbz-amino-2-Boc-amino-butyric acid;Butanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(phenylmethoxy)carbonyl]amino]-;4-(((Benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)butanoic acid
• CAS NO: 47461-65-4
• Molecular Formula: C₁₇H₂₄N₂O₆
• Molecular Weight: 352.38226
• Mol File: 47461-65-4.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Cbz-amino-2-Boc-amino-butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cbz-amino-2-Boc-amino-butyric acid(47461-65-4)
• EPA Substance Registry System: 4-Cbz-amino-2-Boc-amino-butyric acid(47461-65-4)

Safety Data

• Hazardous Substances Data: 47461-65-4(Hazardous Substances Data)

Usage

General Description

4-Cbz-amino-2-Boc-amino-butyric acid is a chemical compound with the molecular formula C17H23N3O4. It is a derivative of amino-butyric acid and contains both a carbobenzyloxy (Cbz) and a tert-butyloxycarbonyl (Boc) protecting groups. 4-Cbz-amino-2-Boc-amino-butyric acid is commonly used in organic synthesis and peptide chemistry as a building block for the synthesis of various peptides and peptidomimetics. It is also used as a substrate for the preparation of unnatural amino acids and pharmaceutical intermediates. The compound is a white to off-white solid and is typically stored and handled under controlled conditions to prevent degradation and ensure its stability.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 95766-36-2 H-A₂bu(Z)-OH 
• 501-53-1 benzyl chloroformate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2130-77-0 (S)-2-Amino-4-benzyloxycarbonylamino-butyric acid 
• 1758-80-1 L-2,4-diaminobutyrate 
• 13726-85-7 Boc-Gln-OH 
• 25691-37-6 (2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid 

Downstream Products

• 22217-93-2 N^α-tert.-Butyloxycarbonyl-N^γ-benzyloxycarbonyl-L-α,γ-diaminobuttersaeure-p-nitro-phenylester 
• 197892-14-1 (S)-benzyl tert-butyl (4-hydroxybutane-1,3-diyl)dicarbamate 
• 378802-38-1 tris[4-(β-benzyloxycarbonylaminomethyl-N-t-butoxycarbonyl-L-alanyl)aminophenyl]methane 
• 1179974-63-0 Boc-Dab(Cbz)-Gly-OtBu 
• 189302-42-9 tert-butyl ester N^α-Boc-N^δ-benzyloxycarbonyl-nor-L-ornithine 
• 1007876-71-2 C₂₈H₃₈N₂O₆S 
• 226212-75-5 methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate 

Relevant articles and documents

Cγ(S/ R)-Bimodal Peptide Nucleic Acids (Cγ- bm-PNA) Form Coupled Double Duplexes by Synchronous Binding to Two Complementary DNA Strands

Peptide nucleic acids (PNAs) are linear equivalents of DNA with a neutral acyclic polyamide backbone that has nucleobases attached via tert-amide link on repeating units of aminoethylglycine. They bind complementary DNA or RNA with sequence specificity to form hybrids that are more stable than the corresponding DNA/RNA self-duplexes. A new type of PNA termed bimodal PNA [Cγ(S/R)-bm-PNA] is designed to have a second nucleobase attached via amide spacer to a side chain at Cγon the repeating aeg units of PNA oligomer. Cγ-bimodal PNA oligomers that have two nucleobases per aeg unit are demonstrated to concurrently bind two different complementary DNAs, to form duplexes from both tert-amide side and Cγside. In such PNA:DNA ternary complexes, the two duplexes share a common PNA backbone. The ternary DNA 1:Cγ(S/R)-bm-PNA:DNA 2 complexes exhibit better thermal stability than the isolated duplexes, and the Cγ(S)-bm-PNA duplexes are more stable than Cγ(R)-bm-PNA duplexes. Bimodal PNAs are first examples of PNA analogues that can form DNA2:PNA:DNA1 double duplexes via recognition through natural bases. The conjoined duplexes of Cγ-bimodal PNAs can be used to generate novel higher-level assemblies.

The Scaffold Design of Trivalent Chelator Heads Dictates Affinity and Stability for Labeling His-tagged Proteins in vitro and in Cells

Small chemical/biological interaction pairs are at the forefront in tracing protein function and interaction at high signal-to-background ratios in cellular pathways. However, the optimal design of scaffold, linker, and chelator head still deserve systematic investigation to achieve the highest affinity and kinetic stability for in vitro and especially cellular applications. We report on a library of N-nitrilotriacetic acid (NTA)-based multivalent chelator heads (MCHs) built on linear, cyclic, and dendritic scaffolds and compare these with regard to their binding affinity and stability for the labeling of cellular His-tagged proteins. Furthermore, we describe a new approach for tracing cellular target proteins at picomolar probe concentrations in cells. Finally, we outline fundamental differences between the MCH scaffolds and define a cyclic trisNTA chelator that displays the highest affinity and kinetic stability of all reported reversible, low-molecular-weight interaction pairs.

Inhibition of glyoxalase I: The first low-nanomolar tight-binding inhibitors

A series of rational modifications to the structure of known S-(N-aryl-N-hydroxycarbamoyl)glutathione-based glyoxalase I inhibitors culminated in the discovery of the first single-digit nanomolar inhibitor. This study makes available key information about possible means to address the issues of metabolic instability, low potency, and synthetic complexicity that have plagued the area of glyoxalase I inhibition. Knowledge garnered from this study has implications in the design of inhibitors with higher conformational definition and lower peptidic character.