42989-85-5

Basic information

• Product Name: (BOC-AMINOOXY)ACETIC ACID
• Synonyms: BOC-(NHOAC)-OH;BOC-NH-O-CH2COOH;BOC-AOA;BOC-AOAC-OH;BOC-AOA-OH;(BOC-AMINOOXY)ACETIC ACID;BOC-3-(AMINOOXY)ACETIC ACID;2-(BOC-AMINOOXY)-ACETIC ACID
• CAS NO: 42989-85-5
• Molecular Formula: C₇H₁₃NO₅
• Molecular Weight: 191.18
• Product Categories: N-BOC;Nitric Oxide Reagents;Cross Linking Reagents;Heterocycles
• Mol File: 42989-85-5.mol

Chemical Properties

• Melting Point: ~115 °C (dec.)
• Appearance: /
• Density: 1.214 g/cm³
• Refractive Index: 1.46
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol.
• PKA: 2.97±0.10(Predicted)
• BRN: 6137646
• CAS DataBase Reference: (BOC-AMINOOXY)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (BOC-AMINOOXY)ACETIC ACID(42989-85-5)
• EPA Substance Registry System: (BOC-AMINOOXY)ACETIC ACID(42989-85-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 42989-85-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(BOC-AMINOOXY)ACETIC ACID is used as a bifunctional linking reagent for the synthesis of complex peptide structures. Its application reason is to facilitate the formation of specific peptide bonds and improve the overall efficiency of the synthesis process.
Used in Chemical Synthesis:
(BOC-AMINOOXY)ACETIC ACID is used as a reagent for introducing a hydroxylamine moiety into peptides. The application reason is to enable the reaction with an aldehyde to form an oxime, which is crucial for the synthesis of certain complex molecules.
Used in Polymer Science:
(BOC-AMINOOXY)ACETIC ACID is used in the preparation of Boc-aminooxy tetra(ethylene glycol). The application reason is to create a versatile building block for the synthesis of various polymers and macromolecules with specific properties and functionalities.
Used in Research and Development:
(BOC-AMINOOXY)ACETIC ACID is used as a research tool for studying the properties and reactivity of hydroxylamine-containing compounds. The application reason is to gain insights into the chemical behavior of these compounds and potentially discover new applications in various fields.

InChI:InChI=1/C7H13NO5/c1-7(2,3)13-6(11)8-12-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)

Upstream product

• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 79-08-3 bromoacetic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 645-88-5 aminooxyacetic acid 
• 136499-22-4 methyl-2-(tert-butoxycarbonylaminooxy)acetate 
• 2921-14-4 (aminooxy)acetic acid hemihydrochloride 

Downstream Products

• 33809-60-8 C₁₄H₂₀N₂O₅ 
• 80366-85-4 N-succinimidyl [[(t-butyloxycarbonyl)amino]oxy]acetate 
• 679406-29-2 2-(N-tert-butoxycarbonyl-aminooxy)-N-(3-benzoyl-phenyl)-acetamide 
• 848349-06-4 C₂₁H₃₀N₂O₆ 
• 934611-66-2 N-[2-(2-aminooxyacetylamino)-ethyl]-N-tert-butoxycarbonyl-3-azido-4-fluorobenzamide 
• 934611-67-3 N-[3-(2-aminooxyacetylamino)-propyl]-N-tert-butoxycarbonyl-3-azido-4-fluorobenzamide 
• 934611-68-4 C₁₈H₂₅FN₆O₅S₂ 
• 679406-28-1 C₁₉H₂₄F₃N₅O₆ 
• 758716-92-6 C₅₇H₉₀N₁₆O₂₁S₃ 
• 1007222-11-8 C₂₁H₃₃N₃O₈ 
• 850256-51-8 C₅₁H₇₆N₁₀O₁₄S 
• 1058165-52-8 tert-butyl 16-(2,4-dinitrophenylamino)-2-oxo-7,10,13-trioxa-3-azahexadecyloxycarbamate 
• 1224728-14-6 C₄₇H₆₀N₆O₉ 
• 293302-29-1 C₁₄H₁₉NO₅ 

Relevant articles and documents

Template Assembled Synthetic Proteins: Condensation of a Multifunctional Peptide to a Topological Template via Chemoselective Ligation

A chemoselective ligation via oxime bond formation is used for the chemical synthesis of template assembled peptides according to the TASP (Template Assembled Synthetic Proteins) approach.Aminooxyacetylation of the multifunctional partial sequence Lys- Arg- Asp- Ser of lactoferrin and subsequent condensation in aqueous solution with a topological template containing four selectively addressable aldehyde functions as attachments sites gives readily access to the TASP molecule. - Keywords: Template Assembled Synthetic Proteins; chemoselecive ligation; multifunctional peptide; topological template; oxime bond formation

Synthesis of an oxyamino-containing phenanthroline derivative for the efficient preparation of phenanthroline oligonucleotide oxime conjugates

A phenanthroline derivative bearing an oxyamino linker was efficiently prepared from commercial 5-nitro-1,10-phenanthroline. The subsequent reaction with an oligonucleotide containing an aldehyde either at the 5′ end or the 3′ end afforded, in good yield, the phenanthroline-oligonucleotide conjugates through oxime bond formation.

A Programmable Signaling Molecular Recognition Nanocavity Prepared by Molecular Imprinting and Post-Imprinting Modifications

Inspired by biosystems, a process is proposed for preparing next-generation artificial polymer receptors with molecular recognition abilities capable of programmable site-directed modification following construction of nanocavities to provide multi-functionality. The proposed strategy involves strictly regulated multi-step chemical modifications: 1) fabrication of scaffolds by molecular imprinting for use as molecular recognition fields possessing reactive sites for further modifications at pre-determined positions, and 2) conjugation of appropriate functional groups with the reactive sites by post-imprinting modifications to develop programmed functionalizations designed prior to polymerization, allowing independent introduction of multiple functional groups. The proposed strategy holds promise as a reliable, affordable, and versatile approach, facilitating the emergence of polymer-based artificial antibodies bearing desirable functions that are beyond those of natural antibodies.

Site-Specific Conjugation of a Radioiodinated Phenethylamine Derivative to a Monoclonal Antibody Results in Increased Radioactivity Localization in Tumor

The preparation of a novel radioiodination reagent, the (aminooxy)acetyl derivative of (p-iodopheny;)ethylamine, is described.Convemtional radioiodination of proteins involves the formation of iodotyrosine residues, but for in vivo applications such as thyroid or stomach immunoscintigraphy, the susceptibility of these residues to tissue dehalogenases constitutes a serious disadvantage.Using our new compound, which has a particularly nonreactive aromatic ring, we confirm and extend studies published by other workers indicating the much greater in vivo stability of iodophenyl compounds compared to the more conventional iodophenolic ones.In addition, the aminoxy group of our reagent gives a stable and specific linkage to aldehyde groups formed by periodate oxidation on the sugar moiety of antibody molecules. in vitro, favorable binding activity and high stability was obtained with ((iodoaryl)aminooxy) labeled monoclonal antibody directed against carcinoembryonic antigen.In vivo, using paired labeling experiments in nude mice bearing colon carcinoma xenografts, the ((iodoaryl)amino)oxy-MAb (MAb=monoclonal antibody) was compared with the same MAb131I-labeled by conventional chloramine-T method.Tumor 125I concentration of (aryloamino)oxy MAb (measured as percent injected dose per gram) was significantly higher as compared to values obtained with a conventionally labeled 131I antibody.Additionally, thyroid uptake, an indicator of iodine release from the antibody, was up to 25 times lower after injection of 125I-MAb obtained by the new method as compared to the conventionally iodinated 131I-MAb.

Conjugation of Aztreonam, a Synthetic Monocyclic β-Lactam Antibiotic, to a Siderophore Mimetic Significantly Expands Activity against Gram-Negative Bacteria

Monocyclic β-lactams with antibiotic activity were first synthesized more than 40 years ago. Extensive early structure-activity relationship (SAR) studies, especially in the 1980s, emphasized the need for heteroatom activation of monocyclic β-lactams and led to studies of oxamazins, monobactams, monosulfactams, and monocarbams with various side chains and peripheral substitution that revealed potent activity against select strains of Gram-negative bacteria. Aztreonam, still the only clinically used monobactam, has notable activity against many Gram-negative bacteria but limited activity against some of the most problematic multidrug resistant (MDR) strains of Pseudomonas aeruginosa and Acinetobacter baumannii. Herein, we report that extension of the side chain of aztreonam is tolerated and especially that coupling of the side chain free acid with a bis-catechol siderophore mimetic significantly improves activity against the MDR strains of Gram-negative bacteria that are of most significant concern.

Synthesis and conformational analysis of an expanded cyclic ketoxime-hexapeptide

In this work the synthesis of a linear hexapeptide with a hydroxylamine functionality at the N-terminus and a ketone instead of the carboxylic acid at the C-terminus is described. Cyclization by ketoxime formation yields the 19-membered ring-expanded cyclic hexapeptide cyclo[Goly-Val-Ala-Pro-Leu-Kly] which adopts a main conformer with two intramolecular hydrogen bonds. The hydrolytic stability of a ketoxime lies between the inert amide and the labile imine. The substitution of an amide bond for an iminium bond transforms the irreversible macrocyclization into a reversible process, but macrocyclic imines are difficult to isolate because they are prone to hydrolysis. The enhanced chemical stability of the ketoxime justifies its application in ligation protocols. The detailed NMR analysis of a ketoxime linkage presented here identifies its local conformational preferences in a constrained peptide environment.

POLYMER ENHANCEMENT OF ENZYMATIC ACTIVITY

Provided herein are methods for enhancing enzymatic activity using certain polymers that may be optionally attached to an enzyme. The polymers may be thermally-responsive polymers, including poly N-isopropylacrylamide or poly N-isopropylmethacrylamide. The polymer may also be a copolymer with at least two different monomer residues. The monomer residues may have a structure of formula (I): wherein R1, RA and RB are as described herein. Examples of such monomer residues may include N-isopropylacrylamide (NIPAm) or N-isopropylmethacrylamide (NIPMa). The polymer may include additional monomer residues, such as aminooxy-bearing methacrylamide monomer residues that can be modified to vary the lower critical solution temperature (LCST) of the polymer.

Stabilization of vesicular and supported membranes by glycolipid oxime polymers

We report herein new synthetic glycolipid dimers and polymers that provide unprecedented stability to both supported (SLBs) and vesicular lipid bilayers against dehydration and serum exposure. These novel physical properties will enable pharmaceutical delivery and development of SLB bioanalytical devices. The Royal Society of Chemistry.

NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS

The invention relates to the use of at least one compound of the formula (I), in which R and R3 are particularly a hydrogen atom, R1 is particularly a hydrogen atom or a methyl, ethyl or isobutyl mi group, R4, R5, R6 and R7 are independently a hydrogen atony, an alkoxyl group with 1 to 7 carbon atoms or a halogen atom, R2 is a hydrogen atom, an O? group or an OH group, B is an N-GP1 or NRc, group, GP1 being a Boc or Cbz group, and Rc is a hydrogen atom or a methyl or t-butyl group, for preparing a drug for treating conditions associated with bacterial infections, in particular for treating bacterial diseases.

MONOBACTAM HYDRAZIDES CONTAINING CATECHOL SULFONIC ACID GROUPS

Antibacterial activity is exhibited by novel compounds having the formula or a pharmaceutically acceptable salt thereof. R3 and R4 are the same or different and each is hydrogen or alkyl or R3 and R4 taken together with the nitrogen atoms to which they are attached form a 1,2-diazacyclobutane, 1,2-diazacyclopentane, 1,2-diazacyclohexane, or 1,2-diazacycloheptane ring. Y1 and Y2 are either hydrogen or OR11 but are not the same. R11 is hydrogen, alkanoyl of from one to ten carbon atoms, substituted alkanoyl of from two to ten carbon atoms, phenylcarbonyl, (substituted phenyl) carbonyl, heteroarylcarbonyl, phenylalkanoyl, (substituted phenyl) alkanoyl, or heteroarylalkanoyl