204711-97-7

Basic information

• Product Name: (S)-N-Boc-2-(4'-pentenyl)glycine
• Synonyms: (S)-N-Boc-2-(4'-pentenyl)glycine;(2S)-2-(Boc-amino)-6-heptenoic acid;Boc-L-2-amino-6-heptenoicacid
• CAS NO: 204711-97-7
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.29944
• Mol File: 204711-97-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-N-Boc-2-(4'-pentenyl)glycine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Boc-2-(4'-pentenyl)glycine(204711-97-7)
• EPA Substance Registry System: (S)-N-Boc-2-(4'-pentenyl)glycine(204711-97-7)

Safety Data

• Hazardous Substances Data: 204711-97-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-N-Boc-2-(4'-pentenyl)glycine is used as a building block for the synthesis of complex pharmaceuticals, as it can be incorporated into the structure of various drugs. Its unique structure and stereochemistry allow for the creation of molecules with specific biological activities and interactions.
Used in Peptide Synthesis:
In the field of peptide chemistry, (S)-N-Boc-2-(4'-pentenyl)glycine is used as a key component in the assembly of peptide sequences. Its presence in a peptide chain can influence the overall properties and functions of the peptide, making it an important compound for the development of novel bioactive peptides.
Used in Material Sciences:
(S)-N-Boc-2-(4'-pentenyl)glycine can also be utilized in the development of new materials with specific properties. Its unique structure and reactivity make it a valuable component in the design and synthesis of advanced materials for various applications, such as in the fields of electronics, coatings, and adhesives.
Used in Research and Development:
As a versatile chemical compound, (S)-N-Boc-2-(4'-pentenyl)glycine is used in research and development for the exploration of new chemical reactions, synthesis methods, and potential applications in various industries. Its unique properties and reactivity make it an attractive candidate for further investigation and development.

Upstream product

• 204711-95-5 [(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-hex-5-enyl]-carbamic acid tert-butyl ester 
• 947608-46-0 2(S)-(acetyl-tert-butoxycarbonylamino)-hept-6-enoic acid ethyl ester 
• 947608-39-1 ethyl 2-acetamidohepta-2,6-dienoate 
• 947608-43-7 C₁₁H₁₉NO₃ 
• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 166734-64-1 (S)-2-amino-hept-6-enoic acid 
• 89985-87-5 methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 102831-44-7 diethyl tert-butoxycarbonylaminomalonate 
• 1150697-16-7 2-tert-butoxycarbonylamino-2-(ethoxycarbonyl)hept-6-enoic acid 
• 119808-35-4 2-tert-butoxycarbonylamino-2-pent-4-enyl-malonic acid diethyl ester 
• 204711-96-6 (2S)-2-[(tert-butoxycarbonyl)amino]-6-heptenoic acid methyl ester 
• 1119-51-3 bromopentene 

Downstream Products

• 1219015-40-3 C₃₃H₄₈N₄O₆ 
• 1219015-36-7 C₄₂H₆₆N₄O₉ 
• 1428535-89-0 thioacetic acid S-[(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-(3-trifluoromethyl-phenylcarbamoyl)-hexyl] ester 
• 329966-94-1 (S)-methyl 7-(tert-butoxycarbonylamino)-8-oxo-8-(phenylamino)octanoate 

Relevant articles and documents

Aliphatic chain-containing macrocycles as diazonamide A analogs

[Figure not available: see fulltext.] Aliphatic alkyl chain-containing 12–14-membered macrocycles have been designed as structural analogs of antimitotic natural product diazonamide A. Macrocycles were synthesized from 5-bromooxazole in 7 to 9 linear step

Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.

Effect of α-Methyl versus α-Hydrogen Substitution on Brain Availability and Tumor Imaging Properties of Heptanoic [F-18]Fluoroalkyl Amino Acids for Positron Emission Tomography (PET)

Two [18F]fluoroalkyl substituted amino acids differing only by the presence or absence of a methyl group on the α-carbon, (S)-2-amino-7-[18F]fluoro-2-methylheptanoic acid ((S)-[18F]FAMHep, (S)-[18F]14) and (S)-2-amino-7-[18F]fluoroheptanoic acid ((S)-[18F]FAHep, (S)-[18F]15), were developed for brain tumor imaging and compared to the well-established system L amino acid tracer, O-(2-[18F]fluoroethyl)-l-tyrosine ([18F]FET), in the delayed brain tumor (DBT) mouse model of high-grade glioma. Cell uptake, biodistribution, and PET/CT imaging studies showed differences in amino acid transport of these tracer by DBT cells. Recognition of (S)-[18F]15 but not (S)-[18F]14 by system L amino acid transporters led to approximately 8-10-fold higher uptake of the α-hydrogen substituted analogue (S)-[18F]15 in normal brain. (S)-[18F]15 had imaging properties similar to those of (S)-[18F]FET in the DBT tumor model while (S)-[18F]14 afforded higher tumor to brain ratios due to much lower uptake by normal brain. These results have important implications for the future development of α-alkyl and α,α-dialkyl substituted amino acids for brain tumor imaging.

Insight into Transannular Cyclization Reactions to Synthesize Azabicyclo[X.Y.Z]alkanone Amino Acid Derivatives from 8-, 9-, and 10-Membered Macrocyclic Dipeptide Lactams

An efficient method for synthesizing different functionalized azabicyclo[X.Y.0]alkanone amino acid derivatives has been developed employing electrophilic transannular cyclizations of 8-, 9-, and 10-membered unsaturated macrocycles to form 5,5-, 6,5-, 7,5-, and 6,6-fused bicylic amino acids, respectively. Macrocycles were obtained by a sequence featuring peptide coupling of vinyl-, allyl-, homoallyl-, and homohomoallylglycine building blocks followed by ring-closing metathesis. X-ray crystallographic analyses of the 8-, 9-, and 10-membered macrocyclic lactam starting materials as well as certain bicyclic amino acid products provided insight into their conformational preferences as well as the mechanism for the diastereoselective formation of specific azabicycloalkanone amino acids by way of transannular iodolactamization reactions. (Chemical Equation Presented).

Bicyclic tetrapeptides as potent HDAC inhibitors: Effect of aliphatic loop position and hydrophobicity on inhibitory activity

Several histone deacetylase (HDAC) inhibiting bicyclic tetrapeptides have been designed and synthesized through intramolecular ring-closing metathesis (RCM) reaction and peptide cyclization. We designed bicyclic tetrapeptides based on CHAP31, trapoxin B a

Flexible synthesis and evaluation of diverse anti-apicomplexa cyclic peptides

A modular approach to synthesize anti-Apicomplexa parasite inhibitors was developed that takes advantage of a pluripotent cyclic tetrapeptide scaffold capable of adjusting appendage and skeletal diversities in only a few steps (one to three steps). The diversification processes make use of selective radical coupling reactions and involve a new example of a reductive carbon-nitrogen cleavage reaction with SmI2. The resulting bioactive cyclic peptides have revealed new insights into structural factors that govern selectivity between Apicomplexa parasites such as Toxoplasma and Plasmodium and human cells.

Design, synthesis, and biological activity of boronic acid-based histone deacetylase inhibitors

Guided by the proposed catalytic mechanism of histone deacetylases (HDACs), we designed and synthesized a series of boronic acid-based HDAC inhibitors bearing an R-amino acid moiety. In this series, compounds (S)-18, 20, and 21 showed potent HDAC-inhibito

Discovery and structure-activity relationship of P1-P 3 ketoamide derived macrocyclic inhibitors of hepatitis C virus NS3 protease

Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, and affects more than 200 million people worldwide. Although combination therapy of interferon-a and ribavirin is reasonably

Application of ring-closing metathesis for the synthesis of macrocyclic peptidomimetics as inhibitors of HCV NS3 protease

An efficient synthetic approach for the preparation of macrocyclic peptidomimetics for inhibition of HCV NS3 is presented. The macrocyclic core is built using ring-closing metathesis (RCM) of a tripeptidic diene. The presented approach allows the introduction of heteroatoms in strategic places along the macrocyclic ring. The methyl ester moiety in the RCM products was synthetically manipulated to install a ketoamide moiety via a Passerini reaction.

Potent inhibitors of the hepatitis C virus NS3 protease: Design and synthesis of macrocyclic substrate-based β-strand mimics

The virally encoded NS3 protease is essential to the life cycle of the hepatitis C virus (HCV), an important human pathogen causing chronic hepatitis, cirrhosis of the liver, and hepatocellular carcinoma. The design and synthesis of 15-membered ring β-strand mimics which are capable of inhibiting the interactions between the HCV NS3 protease enzyme and its polyprotein substrate will be described. The binding interactions between a macrocyclic ligand and the enzyme were explored by NMR and molecular dynamics, and a model of the ligand/enzyme complex was developed.