125414-41-7

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-SERINOL, 97 is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure, including the Boc-protected amine group, makes it a valuable building block in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Synthesis:
In the field of chemical synthesis, N-BOC-SERINOL, 97 serves as a versatile reagent for the creation of a wide range of chemical compounds. The hydroxyl groups present in the molecule allow for further functionalization, making it a useful starting material for the synthesis of complex organic molecules.
Used in Bioconjugation:
N-BOC-SERINOL, 97 is used as a bioconjugation agent for the attachment of biotin to other biomolecules, such as proteins, peptides, or nucleic acids. The biotin present in the molecule can form stable complexes with avidin or streptavidin, enabling the development of bioconjugates for various applications, including diagnostics, drug delivery, and molecular recognition.
Used in Material Science:
In material science, N-BOC-SERINOL, 97 can be utilized as a component in the development of novel materials with specific properties. The ability to modify the hydroxyl groups and the presence of the Boc-protected amine group make it a promising candidate for the creation of materials with tailored characteristics, such as improved biocompatibility, enhanced stability, or specific binding affinities.
Used in Research and Development:
N-BOC-SERINOL, 97 is used as a research tool for studying various biological processes and mechanisms. Its unique structure allows scientists to investigate the effects of biotin and PEG derivatives on cellular processes, protein-protein interactions, and other biological phenomena. N-BOC-SERINOL, 97 can also be employed in the development of new methodologies and techniques in the fields of chemistry, biology, and materials science.

InChI:InChI=1/C8H17NO4/c1-8(2,3)13-7(12)9-6(4-10)5-11/h6,10-11H,4-5H2,1-3H3,(H,9,12)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 534-03-2 serinol 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 2134-29-4 3-Hydroxypropanal 
• 167486-39-7 tert-butyl (1,3-bis(benzyloxy)propan-2-yl)carbamate 
• 166047-30-9 1-benzyl-6-(tert-butoxycarbonylamino)-4-methylhexahydro-1H-1,4-diazepine 
• 213475-74-2 tert-butyl (1,3-diaminopropan-2-yl)carbamate 
• 213475-70-8 methanesulfonic acid 2-tert-butoxycarbonylamino-3-methanesulfonyloxypropylester 
• 186795-56-2 tert-butyl (1-formyl-vinyl)carbamate 

Relevant academic research and scientific papers

Fabrication of eco-friendly nanofibrous membranes functionalized with carboxymethyl-β-cyclodextrin for efficient removal of methylene blue with good recyclability

Considering the excellent thermo-mechanical properties, chemical stability and low cost of biodegradable aliphatic-aromatic copolyesters, they are an ideal matrix when functionalized for capturing pollutants in wastewater. In this work, biodegradable poly((butylene succinate-co-terephthalate)-co-serinol terephthalate) (PBSST) copolyesters with amino side group (-NH2) were first synthesized through copolymerization, followed by grafting carboxymethyl-β-cyclodextrin (CM-β-CD) into PBSST molecular chains via amidation reaction to prepare PBSST-g-β-CD. The corresponding nanofibrous membranes were then fabricated by electrospinning as adsorbents for efficiently removing cationic dye methyl blue (MB) from aqueous solutions. The adsorption performance of the nanofibrous membranes was fitted well with pseudo-second-order model and Langmuir isotherm model. The maximum adsorption capacity was 543.48 mg g?1 for MB along with a removal efficiency of 98% after five regeneration cycles, indicating the high adsorption capacity and good recyclability of nanofibrous membranes. The adsorbents possess features of high adsorption capacity, eco-friendliness and easy operation, and exhibit great potential for disposing of printing-dying wastewater.

Mechanism of Helix Induction on a Stereoregular Poly((4-carboxyphenyl)acetylene) with Chiral Amines and Memory of the Macromolecular Helicity Assisted by Interaction with Achiral Amines

Cis-transoidal poly((4-carboxyphenyl)acetylene) (poly-1) is an optically inactive polymer but forms an induced one-handed helical structure upon complexation with optically active amines such as (R)-(1-(1-naphthyl)ethyl) amine ((R)-2) in DMSO. The complexes show a characteristic induced circular dichroism (ICD) in the UV-visible region of the polymer backbone. Moreover, the macromolecular helicity of poly-1 induced by (R)-2 can be "memorized" even after complete replacement of (R)-2 by various achiral amines. We now report fully detailed studies on the mechanism of the helicity induction and memory of the helical chirality of poly-1 by means of UV-visible, CD, and infrared spectroscopies. We have found that a one-handed helix is cooperatively induced on poly-1 upon the ion pair formation of the carboxy groups of poly-1 with optically active amines and that the bulkiness of the chiral amines plays a crucial role for inducing an excess of a single-handed helix. On the other hand, the free ion formation was found to be essential for the macromolecular helicity memory of poly-1 after the replacement of the chiral amine by achiral amines, since the intramolecular electrostatic repulsion between the neighboring carboxylate ions of poly-1 significantly contributes to reduce the atropisomerization process of poly-1. On the basis of the mechanism of helicity induction and the memory of the helical chirality drawn from the present studies, we succeeded in creating an almost perfect memory of the induced macromolecular helicity of poly-1 with (R)-2 by using 2-aminoethanol as an achiral chaperoning molecule to assist in maintaining the memory of helical chirality.

High Drug Loading, Reversible Disulfide Core-Cross-Linked Multifunctional Micelles for Triggered Release of Camptothecin

Nanomedicines in polymeric therapeutics present a potential treatment for cancers. However, their clinical effectiveness still has room to be improved. Herein, reduction-responsive reversibly core-cross-linked micelles based on the poly(ethylene glycol)-dihydrolipoic acid (MeO-PEG2k-DHLA) conjugate were developed for triggered intracellular release of camptothecin (CPT). Coupling two molecules of dihydrolipoic acid (DHLA) to methyl-terminated PEG (Mw 2000) through a labile ester bond was performed by solution-phase condensation reaction. Due to the amphiphilic property, the MeO-PEG2k-DHLA conjugate formed micelles that were readily cross-linked with disulfide formation dispersed in water. These sole cross-linked micelles were 74.9 nm in hydrodiameter, as analyzed by dynamic light scattering (DLS). The nanostructures demonstrated excellent stability against extensive dilution, while rapidly dissociating under 10 mM glutathione (GSH), highlighting their potential for drug delivery. Interestingly, CPT was modified with a disulfide linkage and subsequently conjugated to the MeO-PEG2k-DHLA polymer scaffold. Core-cross-linking of the micelles achieved high drug loading of CPT (31.81%, wt %) and demonstrated that CPT release at pH 7.4 was significantly declined by cross-linking (i.e., less than 15% release in 24 h), whereas more than 90% of CPT was released under 10 mM GSH condition. In vitro cellular uptake and MTT assays showed that CPT-conjugated MeO-PEG2k-DHLA micelles were effectively internalized into tumor cells to induce the cytotoxic effects against HepG-2 and MCF-7 cells. Importantly, in vivo pharmacokinetics analysis demonstrated the nanoscale feature of micelles makes CPT to present longer retention time, resulting in a higher accumulation at tumor sites. Taken together, the disulfide core-cross-linked MeO-PEG2k-DHLA multifunctional micelles with high drug loading and excellent stability are potential candidates for tumor-targeting drug delivery.

Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst

A simple, rapid, and efficient protocol for the chemoselective N-Boc protection of amines using sulfamic acid as catalyst is described. N-Boc protection of various structurally diverse aliphatic, aromatic, alicyclic, and heterocyclic amines (1°, 2°, 3°) was carried out with (Boc)2O using sulfamic acid as catalyst (5 mol %) at room temperature under solventless conditions. The advantages of this method are simplicity, shorter reaction times (1-15 min), a cost-effective catalyst, and excellent isolated yields (90-100%); it is also environmentally benign. Moreover, the combined use of ultrasound and sulfamic acid achieves a synergic effect that is especially marked in the N-Boc protection of deactivated (sterically hindered and electron-deficient) amines. The catalyst possesses distinct advantages: ease of handling, cleaner reactions, high activity, and excellent chemoselectivity.

Immucillins in custom catalytic-site cavities

Neighboring-group participation in the reaction catalyzed by purine nucleoside phosphorylase involves a compression mode between the 5′- and 4′-ribosyl oxygens, facilitated by His257. The His257Gly mutant opens a space in the catalytic site. Hydrophobic 5′-substituted Immucillins are transition-state analogue inhibitors of this mutant enzyme. Dissociation constants as low as 2 pM are achieved, with Km/Kd as high as 400,000,000.

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU): A new reagent for the cleavage of tetrahydropyranyl, silyl and 4,4'- dimethoxytrityl ethers

A new reagent for the cleavage of tetrahydropyranyl, silyl and 4,4'- dimethoxytrityl ethers is described.

Multimerization increases tumor enrichment of peptide–photosensitizer conjugates

Photodynamic therapy (PDT) is an established therapeutic modality for the management of cancers. Conjugation with tumor-specific small molecule ligands (e.g., short peptides or peptidomimetics) could increase the tumor targeting of PDT agents, which is ve

Y-shaped block copolymer (methoxy-poly(ethylene glycol))2-b-poly(l-glutamic acid): Preparation, self-assembly, and use as drug carriers

Y-shaped amphiphilic block copolymers, (methoxy-poly(ethylene glycol))2-block-poly(l-glutamic acid) ((mPEG)2-PGA) and its precursor (methoxy-poly(ethylene glycol)2-block-poly(γ-benzyl-l-glutamate) ((mPEG)2-PBG), were prepared in three steps: (1) macroinitiator (methoxy-poly(ethylene glycol))2-NH2((mPEG)2-NH2) was synthesized by coupling two methoxy-poly(ethylene glycol)s with serinol and diisocyanate. (2) (mPEG)2-PBG was synthesized by ring opening polymerization of γ-benzyl-l-glutamate-N-carboxyanhydride initiated with the macroinitiator ((mPEG)2-NH2); (3) the protective benzyl groups in (mPEG)2-PBG were removed to obtain (mPEG)2-PGA. The properties of both (mPEG)2-PBG and (mPEG)2-PGA were characterized by 1H NMR, FT-IR, GPC, and DLS. In aqueous solution (mPEG)2-PBG tends to form more stable micelles compared to linear mPEG-PBG copolymer. The size of (mPEG)2-PBG decreases with increasing length of hydrophobic PBG in (mPEG)2-PBG. Paclitaxel and cisplatin were grafted onto (mPEG)2-PGA to form (mPEG)2-PGA-PTX (MPTX) with a grafting ratio of near 90% and (mPEG)2-PGA-Pt (MPt) conjugates with a loading efficacy of 15% (w/w). MPTX can greatly improve the solubility of PTX. Both conjugates can self-assemble into micelles with a mean diameter of about 50 nm and show enhanced anti-cancer activity against MCF-7, HeLa, and SMMC cell lines. The in vivo anticancer evaluation in mice shows MPt showed a desirable antitumor activity and allowed us to deduce the system toxicity. Therefore, both MPTX and MPt have a great potential as a polymer drug in cancer chemotherapy. This journal is

Design and Synthesis of Galactose-Biotin Lipid Materials for Liposomes to Promote the Hepatoma Cell–Targeting Effect

A series of novel low-toxic hepatoma cell–targeting lipid materials were designed and synthesized, in which monogalactose, digalactose, and galactose-biotin were used as targeting moieties and hydrophilic heads while stearate was used as hydrophobic tail (Mono-Gal-ST, Di-Gal-ST, and Gal-Biotin-ST). The corresponding galactose-biotin-modified liposomes (Mono-Gal-LPs, Di-Gal-LPs, and Gal-Biotin-LPs) and conventional liposomes (LPs) were prepared. These galactose-biotin-modified liposomes can distinguish hepatoma cells from other tissue cells owing to the recognition of asialoglycoprotein receptor by galactose group. Moreover, the ability of liposomes to distinguish hepatoma cells from normal hepatocytes follows a trend of LPs Mono-Gal-LPs Di-Gal-LPs Gal-Biotin-LPs, which is attributed to the cluster glycoside effect and the synergistic effect of galactose and biotin. In addition, the endocytosis of these galactose-biotin-modified liposomes were competitively inhibited by galactose, further confirming these liposomes entered hepatoma cells via asialoglycoprotein receptor–mediated pathway.

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

Specialized cellular networks of oxidoreductases coordinate the dithiol/disulfide-exchange reactions that control metabolism, protein regulation, and redox homeostasis. For probes to be selective for redox enzymes and effector proteins (nM to μM concentrations), they must also be able to resist non-specific triggering by the ca. 50 mM background of non-catalytic cellular monothiols. However, no such selective reduction-sensing systems have yet been established. Here, we used rational structural design to independently vary thermodynamic and kinetic aspects of disulfide stability, creating a series of unusual disulfide reduction trigger units designed for stability to monothiols. We integrated the motifs into modular series of fluorogenic probes that release and activate an arbitrary chemical cargo upon reduction, and compared their performance to that of the literature-known disulfides. The probes were comprehensively screened for biological stability and selectivity against a range of redox effector proteins and enzymes. This design process delivered the first disulfide probes with excellent stability to monothiols yet high selectivity for the key redox-Active protein effector, thioredoxin. We anticipate that further applications of these novel disulfide triggers will deliver unique probes targeting cellular thioredoxins. We also anticipate that further tuning following this design paradigm will enable redox probes for other important dithiol-manifold redox proteins, that will be useful in revealing the hitherto hidden dynamics of endogenous cellular redox systems.