7750-42-7

Usage

Uses

Used in Pharmaceutical Industry:
Boc-Lys-OtBu.HCl is used as a key intermediate in the synthesis of Tetrahydroisoquinoline derivatives, which are valuable as blood coagulation factor inhibitors. These inhibitors are essential in the development of therapeutic agents for the treatment of thromboembolic disorders, a group of conditions characterized by the formation of blood clots within the circulatory system. By inhibiting blood coagulation factors, Tetrahydroisoquinoline derivatives can help prevent the formation of these clots and alleviate the associated health risks.

Upstream product

• 135727-85-4 N²-[(1,1-dimethylethoxy)carbonyl]-N⁶-[(phenylmethoxy)carbonyl]-L-lysine 1,1-dimethylethyl ester 
• 7750-45-0 5-(S)-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]pentylammonium chloride 
• 13734-28-6 Boc-Lys-OH 
• 75-65-0 tert-butyl alcohol 
• 189279-95-6 (S)-t-Boc-Lys(Bz)-O-t-Bu 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 86060-82-4 Fmoc-Lys(Z)-OH 
• 2389-45-9 Boc-Lys(Z)-OH 
• 63628-63-7 Nε-benzyloxycarbonyl-L-lysine tert-butyl ester 
• 5978-22-3 N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 260783-38-8 tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-azaundecanoate 
• 781661-63-0 2-tert-butoxycarbonylamino-6-(4-nitro-benzenesulfonylamino)-hexanoic acid tert-butyl ester 
• 888949-92-6 tert-butyl (2S)-2-tert-butoxycarbonylamino-6-[3-(4-methoxyphenyl)oxaziridin-2-yl]hexanoate 
• 1027089-85-5 (S)-3-Methyl-2-{(S)-2-[(S)-6-nitro-2-(2-trimethylsilanyl-ethoxycarbonylamino)-hexanoylamino]-3-phenyl-propionylamino}-butyric acid methyl ester 
• 781661-66-3 6-(benzyloxycarbonylmethyl-amino)-2-tert-butoxycarbonylamino-hexanoic acid tert-butyl ester 
• 781661-58-3 6-[benzyloxycarbonylmethyl-(4-nitro-benzenesulfonyl)-amino]-2-tert-butoxycarbonylamino-hexanoic acid tert-butyl ester 
• 218966-06-4 (S)-2-amino-N^α-(tert-butyloxycarbonyl)-6-(8'-O-benzyl-5'-carbaisoalloxazin-10'-yl)hexanoic acid tert-butyl ester 
• 1204482-70-1 tert-butyl N₂-(tert-butoxycarbonyl)-N₆-((R)-(+)-2-tert-butoxycarbonylamino-3-(tritylthio)-propanoyl)lysinate 
• 1204482-72-3 tert-butyl N₂-(tert-butoxycarbonyl)-N₆-((S)-(-)-2-tert-butoxycarbonylamino-3-(tritylthio)-propanoyl)lysinate 
• 1269620-19-0 (S)-tert-butyl 6-((R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanamido)-2-((tert-butoxycarbonyl)amino)hexanoate 

Relevant academic research and scientific papers

Identification of Cyclopropane Formation in the Biosyntheses of Hormaomycins and Belactosins: Sequential Nitration and Cyclopropanation by Metalloenzymes

Hormaomycins and belactosins are peptide natural products that contain unusual cyclopropane moieties. Bioinformatics analysis of the corresponding biosynthetic gene clusters showed that two conserved genes, hrmI/belK and hrmJ/belL, were potential candidates for catalyzing cyclopropanation. Using in vivo and in vitro assays, the functions of HrmI/BelK and HrmJ/BelL were established. HrmI and BelK, which are heme oxygenase-like dinuclear iron enzymes, catalyze oxidation of the ?-amino group of l-lysine to afford l-6-nitronorleucine. Subsequently, HrmJ and BelL, which are iron- and α-ketoglutarate-dependent oxygenases, effectively convert l-6-nitronorleucine into 3-(trans-2-nitrocyclopropyl)-alanine through C4?C6 bond installation. These observations disclose a novel pathway of cyclopropane ring construction and exemplify the new chemistry involving metalloenzymes in natural product biosynthesis.

Short self-assembling peptides with a urea bond: A new type of supramolecular peptide hydrogel materials

There is an increasing need to develop short self-assembling peptides (SAPs) that can form hydrogels for cell engineering and biomedical applications. In this study, we proposed new short self-assembling peptides with a symmetric structure via a urea bond

Non-natural amino acid and application thereof in protein site-specific modification and protein interaction

The invention relates to a non-natural amino acid compound represented by a general formula (I) and a preparation method thereof, and applications of the non-natural amino acid compound in fixed-pointmodification of bio-macro-molecular proteins, protein i

METHODS OF PREPARING N6-((2-AZIDOETHOXY)CARBONYL)LYSINE

Disclosed herein are methods of preparing N6-((2-azidoethoxy)carbonyl)lysine, N6-((2-azidoethoxy)carbonyl)-L-lysine, and N6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N2-(tert-butoxycarbonyl)-N6-((2-chloroethoxy)carbonyl)-L-lysinate and tertbutyl N6-((2-azidoethoxy)carbonyl)-N2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.

Biofunctional supramolecular hydrogels fabricated from a short self-assembling peptide modified with bioactive sequences for the 3D culture of breast cancer MCF-7 cells

Self-assembling peptides are a type of molecule with promise as scaffold materials for cancer cell engineering. We have reported a short self-assembling peptide, (FFiK)2, that had a symmetric structure connected via a urea bond. In this study, we functionalized (FFiK)2 by conjugation with various bioactive sequences for the 3D culture of cancer cells. Four sequences, RGDS and PHSRN derived from fibronectin and AG73 and C16 derived from laminin, were selected as bioactive sequences to promote cell adhesion, proliferation or migration. (FFiK)2, and its derivatives could co-assemble into supramolecular nanofibers displaying bioactive sequences and form hydrogels. MCF-7 cells were encapsulated in functionalized peptide hydrogels without significant cytotoxicity. Encapsulated MCF-7 cells proliferated under 3D culture conditions. MCF-7 cells proliferated with spheroid formation in hydrogels that displayed RGDS or PHSRN sequences, which will be able to be applied to drug screening targeting cancer stem cells. On the other hand, since MCF-7 cells migrated in a 3D hydrogel that displayed AG73, we could construct the metastatic model of breast cancer cells, which is helpful for the elucidation of breast cancer cells and drug screening against cancer cells under metastatic state. Therefore, functionalized (FFiK)2 hydrogels with various bioactive sequences can be used to regulate cancer cell function for tumor engineering and drug screening.

Bioorthogonal Ligation and Cleavage by Reactions of Chloroquinoxalines with ortho-Dithiophenols

A bioorthogonal ligation and cleavage method via reactions of chloroquinoxalines (CQ) and ortho-dithiophenols (DT) is presented. Double nucleophilic substitutions of ortho-dithiophenols to chloroquinoxalines provide conjugates containing tetracyclic benzo[5,6][1,4]dithiino[2,3-b]quinoxaline with strong built-in fluorescence together with release of the other functional molecules. Three cleavable linkers were designed and successfully used in release of the molecules containing biotin from the protein conjugates. The CQ-DT bioorthogonal reactions can be applied for the bioorthogonal ligations, bioorthogonal cleavages, and trans-tagging of proteins, and show advantages of readily accessible unnatural orthogonal groups, appealing reaction kinetics (k2≈1.3 m?1 s?1), excellent biocompatibility of orthogonal groups, and high stability of conjugates. This complements previous bioorthogonal reactions and is a new route for protein-fishing applications and in-gel fluorescence analysis.

Antitumor agents 7. Synthesis, antiproliferative activity and molecular modeling of new L-lysine-conjugated pyridophenoxazinones as potent DNA-binding ligands and topoisomerase IIα inhibitors

A series of L-lysine-conjugated pyridophenoxazinones 2–5 and 2′-5′ were designed and synthesized for developing compounds with multimodal anticancer potentialities. All compounds inhibited the proliferation of a panel of human liquid and solid neoplastic

SWCNT-porphyrin nano-hybrids selectively activated by ultrasound: an interesting model for sonodynamic applications

Sonodynamic therapy (SDT) is an innovative anticancer approach, based on the excitation of a given molecule (usually a porphyrin) by inertial acoustic cavitation that leads to cell deathviathe production of reactive oxygen species (ROS). This study aims t

Structural Basis for Genetic-Code Expansion with Bulky Lysine Derivatives by an Engineered Pyrrolysyl-tRNA Synthetase

Yanagisawa et al. analyzed the Y306A/Y384F mutant of Methanosarcina mazei pyrrolysyl-tRNA synthetase (PylRS) with 17 non-natural, bulky oxycarbonyllysine derivatives for tRNAPyl aminoacylation and site-specific incorporation into proteins. Fourteen crystal structures of the amino acid-bound PylRS mutant revealed the structural bases of the binding. This information facilitates the structure-based design of novel amino acids. Pyrrolysyl-tRNA synthetase (PylRS) and tRNAPyl have been extensively used for genetic-code expansion. A Methanosarcina mazei PylRS mutant bearing the Y306A and Y384F mutations (PylRS(Y306A/Y384F)) encodes various bulky non-natural lysine derivatives by UAG. In this study, we examined how PylRS(Y306A/Y384F) recognizes many amino acids. Among 17 non-natural lysine derivatives, N?-(benzyloxycarbonyl)lysine (ZLys) and 10 ortho/meta/para-substituted ZLys derivatives were efficiently ligated to tRNAPyl and were incorporated into proteins by PylRS(Y306A/Y384F). We determined crystal structures of 14 non-natural lysine derivatives bound to the PylRS(Y306A/Y384F) catalytic fragment. The meta- and para-substituted ZLys derivatives are snugly accommodated in the productive mode. In contrast, ZLys and the unsubstituted or ortho-substituted ZLys derivatives exhibited an alternative binding mode in addition to the productive mode. PylRS(Y306A/Y384F) displayed a high aminoacylation rate for ZLys, indicating that the double-binding mode minimally affects aminoacylation. These precise substrate recognition mechanisms by PylRS(Y306A/Y384F) may facilitate the structure-based design of novel non-natural amino acids.

Preparation method of furosine and salt thereof

The invention relates to a preparation method of furosine and salt thereof. The method comprises steps as follows: 1) a compound in a formula (V) and alcohol react, and a compound in a formula (VI) isobtained; 2) the compound in the formula (VI) reacts with 2-halogenated acetylfuran, and a compound in a formula (III) is obtained; 3) the compound in the formula (III) is subjected to acid hydrolysis, and furosine or salt thereof is obtained, wherein R is C1-6 alkyl, R1 is an amino protection group (such as t-butyloxycarbonyl Boc) and X is halogen. The method is simple and convenient and raw materials are easy to obtain.