3350-20-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-Cbz-amino-2-Boc-amino-butyric acid is used as a key intermediate in the synthesis of complex peptides and proteins for various pharmaceutical applications. Its role is pivotal in the development of drugs that target specific biological pathways, potentially leading to the creation of novel therapeutic agents.
Used in Organic Chemistry Research:
In the realm of organic chemistry, (S)-4-Cbz-amino-2-Boc-amino-butyric acid is utilized as a research tool to explore new synthetic routes and methodologies. Its unique structure allows chemists to investigate the properties and reactivity of protected amino acids, contributing to the advancement of chemical synthesis techniques.
Used in Biochemistry and Molecular Biology:
(S)-4-Cbz-amino-2-Boc-amino-butyric acid is employed in the study of protein structure and function, as well as in the development of bioactive molecules with specific biological activities. Its incorporation into peptides and proteins can provide insights into their folding, stability, and interactions with other biomolecules, furthering our understanding of biological systems.

Upstream product

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

Downstream Products

• 85676-36-4 Boc-Dab(Z)-Tyr-OBzl 
• 84983-59-5 Boc-Dab(Z)-Ser-OMe 
• 22217-93-2 N^α-tert.-Butyloxycarbonyl-N^γ-benzyloxycarbonyl-L-α,γ-diaminobuttersaeure-p-nitro-phenylester 
• 383174-71-8 ethyl (4S)-6-(benzyloxycarbonyl)amino-4-(tert-butoxycarbonyl)amino-3-oxohexanoate 
• 378802-38-1 tris[4-(β-benzyloxycarbonylaminomethyl-N-t-butoxycarbonyl-L-alanyl)aminophenyl]methane 
• 1221795-49-8 Boc-Dab(Z)-OTce 
• 499775-17-6 [(2R,5R)-5-(3-Benzyloxycarbonylamino-propyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester 
• 499775-18-7 3-[(2S,5S)-5-(2-Benzyloxycarbonylamino-ethyl)-3,6-dioxo-piperazin-2-yl]-propionic acid benzyl ester 
• 499775-21-2 [(2R,5S)-5-(2-Benzyloxycarbonylamino-ethyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester 
• 499775-20-1 [(2S,5S)-5-(2-Benzyloxycarbonylamino-ethyl)-3,6-dioxo-piperazin-2-yl]-acetic acid benzyl ester 

Relevant academic research and scientific papers

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.

Influence of pendant chiral Cγ-(alkylideneamino/guanidino) cationic side-chains of PNA backbone on hybridization with complementary DNA/RNA and cell permeability

Intrinsically cationic and chiral Cγ-substituted peptide nucleic acid (PNA) analogues have been synthesized in the form of γ(S)-ethyleneamino (eam)- and γ(S)-ethyleneguanidino (egd)-PNA with two carbon spacers from the backbone. The relative stabilization (ΔTm) of duplexes from modified cationic PNAs as compared to 2-aminoethylglycyl (aeg)-PNA is better with complementary DNA (PNA:DNA) than with complementary RNA (PNA:RNA). Inherently, PNA:RNA duplexes have higher stability than PNA:DNA duplexes, and the guanidino PNAs are superior to amino PNAs. The cationic PNAs were found to be specific toward their complementary DNA target as seen from their significantly lower binding with DNA having single base mismatch. The differential binding avidity of cationic PNAs was assessed by the displacement of DNA duplex intercalated ethidium bromide and gel electrophoresis. The live cell imaging of amino/guanidino PNAs demonstrated their ability to penetrate the cell membrane in 3T3 and MCF-7 cells, and cationic PNAs were found to be accumulated in the vicinity of the nuclear membrane in the cytoplasm. Fluorescence-activated cell sorter (FACS) analysis of cell permeability showed the efficiency to be dependent upon the nature of cationic functional group, with guanidino PNAs being better than the amino PNAs in both cell lines. The results are useful to design new biofunctional cationic PNA analogues that not only bind RNA better but also show improved cell permeability. (Graph Presented).

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.

Quinazoline derivatives useful in cancer treatment

The present invention provides compounds of Formula I (wherein R1, R2, R3, L, and X are as defined herein). [image] or a pharmaceutically acceptable salt, solvate or ester thereof. The present invention also provides compositions comprising these compound

Studies on the mechanism of 1,2-dihydropyrazin-2-one ring formation from dipeptidyl chloromethyl ketone and its chemical properties: Immediate deamination during catalytic hydrogenation

1,2-Dihydropyrazin-2-one derivatives, which have two aminoalkyl groups at the positions 3 and 6, were found to be efficient tools for the construction of potent, selective and long-acting opioid mimetics. During the course of preparation, we found that the catalytic hydrogenation of 3,6- bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove the benzyloxycarbonyl groups resulted in a side reaction. By MS and NMR studies and by preparation of additional 1,2-dihydropyrazin-2-one derivatives, the structure of the by-product was identified as 3-aminomethyl-5,6-dimethyl-1,2- dihydropyrazin-2-one. Preparation of additional compounds substituted with deuterium provided us with sufficient information to confirm the structure of the product and to support a cyclization mechanism in its formation.

γ-amino-substituted analogues of 1-[(S)-2,4-diaminobutanoyl]piperidine as highly potent and selective dipeptidyl peptidase II inhibitors

Using 1-[(S)-2,4-diaminobutanoyl]piperidine as lead compound, we developed a large series of highly potent and selective dipeptidyl peptidase II (DPP II) inhibitors. γ-Amino substitution with arylalkyl groups, for example, a 2-chlorobenzyl moiety, resulted in a DPP II inhibitor with an IC50 = 0.23 nM and a high selectivity toward DPP IV (IC50 = 345 μM). Furthermore, it was shown that the basicity of the γ-amino is important and that α-amino substitution is not favorable. Piperidine-2-nitriles did not show an increase in potency but rather reduced the selectivity. Introduction of a 4-methyl or a 3-fluorine on piperidine improved selectivity and preserved the high potency.