3017-32-1

Basic information

• Product Name: (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate
• Synonyms: (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate
• CAS NO: 3017-32-1
• Molecular Weight: 260.334
• Mol File: 3017-32-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate(3017-32-1)
• EPA Substance Registry System: (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate(3017-32-1)

Safety Data

• Hazardous Substances Data: 3017-32-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate is used as a building block in organic synthesis for [application reason] its ability to contribute to the formation of complex molecular structures.
Used in Peptide Chemistry:
In peptide chemistry, (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate is used as a reagent for [application reason] its capacity to facilitate the synthesis of peptide bonds and the development of peptide-based compounds.
Used in Pharmaceutical Production:
(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate is utilized in the production of pharmaceuticals and bioactive compounds as [application type] a key intermediate for [application reason] its potential to enhance the properties and effectiveness of various medications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate is used as a compound in drug discovery and development for [application reason] its potential to contribute to the creation of novel therapeutic agents.
Used in Drug Discovery:
(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate is employed in drug discovery as a starting material for [application reason] its potential to lead to the development of new drugs with various biological activities.
Used in Antimicrobial Applications:
(S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate has been studied for its potential antimicrobial properties and is used as an active compound in [application type] antimicrobial agents for [application reason] its ability to combat various microorganisms.
Used in Antitumor Applications:
Additionally, (S)-methyl 2-amino-6-(tert-butoxycarbonylamino)hexanoate is used in the development of antitumor agents for [application reason] its potential to exhibit antitumor activities, which could be beneficial in the treatment of cancer.

Upstream product

• 2212-76-2 N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-L-lysine dicyclohexylamine salt 
• 67-56-1 methanol 
• 2418-95-3 (S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid 
• 657-27-2 L-Lysine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13515-95-2 lysine methyl ester dihydrochloride 
• 71989-26-9 Fmoc-Lys(tert-butoxycarbonyl) 
• 14511-39-8 2(S)-2-amino-6-(benzylideneamino)hexanoic acid 
• 2212-75-1 N₂-[(benzyloxy)carbonyl]-L-lysine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2389-60-8 Z-Lys(Boc)-OH 
• 172846-56-9 methyl N²-(((9H-fluoren-9-yl)methoxy)carbonyl)-N⁶-(tert-butoxycarbonyl)-L-lysinate 
• 327026-75-5 Psoc-Lys(Boc)-OMe 
• 2389-49-3 N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester 

Downstream Products

• 10342-42-4 (NFS)-Lys-(Boc)-Lys-(Boc)-OMe 
• 305647-02-3 (S)-6-tert-Butoxycarbonylamino-2-[(E)-3-(3-phenoxy-phenyl)-allylamino]-hexanoic acid methyl ester 
• 247204-57-5 (S)-2-{Bis-[(E)-3-(3-phenoxy-phenyl)-allyl]-amino}-6-tert-butoxycarbonylamino-hexanoic acid methyl ester 
• 327026-75-5 Psoc-Lys(Boc)-OMe 
• 1202655-26-2 C₃₅H₅₇N₅O₁₀S 
• 1202655-02-4 C₂₆H₄₃N₃O₈S 
• 1202655-03-5 C₃₂H₄₇N₃O₈S 
• 1202655-10-4 C₂₅H₄₁N₃O₇S 
• 1202655-18-2 C₂₅H₄₁N₃O₇S 
• 687-64-9 L-lysine methyl ester 

Relevant articles and documents

Investigating a Boronate-Affinity-Guided Acylation Reaction for Labelling Native Antibodies

The excellent molecular recognition capabilities of monoclonal antibodies (mAbs) have opened up exciting opportunities for biotherapeutic discovery. Taking advantage of the full potential of this tool necessitates affinity ligands capable of conjugating directly with small molecules to a defined degree of biorthogonality, especially when modifying natural Abs. Herein, a bioorthogonal boronate-affinity-based Ab ligand featuring a 4-(dimethylamino)pyridine and an S-aryl thioester to label full-length Abs is reported. The photoactivatable linker in the acyl donor facilitated purification of azide-labelled Ab (N3-Ab) was quantitatively cleaved upon brief exposure to UV light while retaining the original Ab activity. Click reactions enabled the precise addition of biotin, a fluorophore, and a pharmacological agent to the purified N3-Abs. The resulting immunoconjugate showed selectivity against targeted cells. Bioorthogonal traceless design and reagentless purification allow this strategy to be a powerful tool to engineer native antibodies amenable to therapeutic intervention.

Epoc group: Transformable protecting group with gold(iii)-catalyzed fluorene formation

This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems. This journal is

Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates

A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H2 followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide-platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.

KETONE INHIBITORS OF LYSINE GINGIPAIN

The present invention provides compounds according to Formula (I) as described herein, and their use for inhibiting the lysine gingipain protease (Kgp) from the bacterium Porphyromonas gingivalis. Also described are gingipain activity probe compounds and methods for assaying gingipain activity are also described, as well as methods for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease.

Simple and efficient Fmoc removal in ionic liquid

A mild method for an efficient removal of the fluorenylmethoxycarbonyl (Fmoc) group in ionic liquid was developed. The combination of a weak base such as triethylamine and [Bmim][BF4] makes the entire system more efficient for the cleavage at room temperature of various amines and amino acid methyl esters in short reaction times. The procedure works well even in the case of N-Fmoc amino acids bearing acid-sensitive protecting groups and of N-alkylated amino acid methyl esters. The solvent-free condition provides a complementary method for Fmoc deprotection in solution phase peptide synthesis and modern organic synthesis.

Radical arylation of tyrosine residues in peptides

The radical arylation of the phenolic side chain of tyrosine in peptides was investigated. Aryl radicals were generated from aryldiazonium salts using titanium(III) chloride as stoichiometric reductant. Due to the high selectivity with which 3-aryltyrosine derivatives were formed, this reaction type represents a new strategy for the direct functionalization of peptides.

Synthesis and antibacterial activities of amphiphilic neomycin B-based bilipid conjugates and fluorinated neomycin B-based lipids

Investigating the effect of lipid hydrophobicity on the activity of amphiphilic neomycin B conjugates, six polycationic amphiphiles (PAs) were created. Four of the new compounds incorporated either palmitic or arachidic di-lipid lysine tails, while two had single fluorinated undecanoic acid tails. The basicity of half of the compounds was increased through the incorporation of six guanidine moieties, in order to assess the effect of base strength on antimicrobial activity. A panel of ten bacteria was used for the testing, with seven strains obtained from the American Type Culture Collection series and three clinical isolates from Canadian Intensive Care Units. When compared to previous results with hydrocarbon monolipids the PAs all compounds were found to have reduced activity, though the hemolytic activity of the compounds with fluorinated tails was sharply reduced, with only a moderate reduction in antimicrobial activity.

MODULATORS OF PHARMACOKINETIC PROPERTIES OF THERAPEUTICS

The present application provides for a compound of Formula I, or a pharmaceutically acceptable salt, solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods and include the administration of such compounds with at least one additional therapeutic agent.

2,2-Dimethyl-2-(o-nitrophenyl)acetyl (DMNA) as an assisted cleavage protecting group for amines

2,2-Dimethyl-2-(o-nitrophenyl)acetyl group (DMNA) was explored as an assisted cleavage protecting group for amines and a one-step deprotection condition was developed for its efficient removal using hydrogenation in the presence of Pd-C or PtO2 catalyst and 10% HOAc in MeOH. DMNA was found to be especially useful for the synthesis of gem-diamino compounds using Hofmann rearrangement.

The (2-phenyl-2-trimethylsilyl)ethoxycarbonyl (Psoc) group - A novel amino protecting group

A novel silicon containing protecting group has been developed based on the known 2-(trimethylsilyl)ethyl system. The new protecting group is cleaved under very mild conditions by treatment with tetra-n-butylammonium fluoride in CH2Cl2 much more rapidly than the 2-(trimethylsilyl)ethoxycarbonyl group, leading to less side reactions.