13650-73-2

Basic information

• Product Name: BOC-SER(BZL)-OSU
• Synonyms: N-alpha-t-Butyloxycarbonyl-O-benzyl-L-serine succinimidyl ester;BOC-O-BENZYL-L-SERINE-HYDROXYSUCCINIMIDESTER;Boc-Ser(OBzl)-OSu;N-Boc-O-benzyl-L-serine N-Succinimidyl Ester Boc-Ser(Bzl)-OSu;CarbaMic acid, [(1S)-2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxo-1-[(phenylMethoxy)Methyl]ethyl]-, 1,1-diMethylethyl ester;tert-butyl (1S)-1-[(benzyloxy)Methyl]-2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethylcarbaMate;N-(tert-Butoxycarbonyl)-O-benzyl-L-serine N-Succinimidyl Ester;Boc-Ser(Bzl)-OSu≥ 97% (HPLC)
• CAS NO: 13650-73-2
• Molecular Formula: C₁₉H₂₄N₂O₇
• Molecular Weight: 392.4
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides
• Mol File: 13650-73-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 106.0 to 110.0 °C
• Appearance: White to off-white/Powder
• Density: 1.28g/cm3
• Refractive Index: 1.556
• Storage Temp.: −20°C
• PKA: 10.28±0.46(Predicted)
• CAS DataBase Reference: BOC-SER(BZL)-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-SER(BZL)-OSU(13650-73-2)
• EPA Substance Registry System: BOC-SER(BZL)-OSU(13650-73-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 13650-73-2(Hazardous Substances Data)

Usage

Description

BOC-SER(BZL)-OSU, also known as Boc-Serine Benzyl Ester p-Toluenesulfonate, is a synthetic reagent used in the field of biochemistry and molecular biology. It is a white to off-white powder with specific chemical properties that make it valuable for research purposes. The compound is particularly useful for studying pyrimidine-based inhibitors of class II aminoacyl-tRNA synthetases, which are essential enzymes in the process of protein synthesis.

Uses

Used in Biochemical Research:
BOC-SER(BZL)-OSU is used as a research reagent for studying pyrimidine-based inhibitors of class II aminoacyl-tRNA synthetases. Its application in this field is crucial for understanding the mechanisms of protein synthesis and the role of these enzymes in cellular processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, BOC-SER(BZL)-OSU is used as a key intermediate in the synthesis of various drugs targeting class II aminoacyl-tRNA synthetases. By understanding the interactions between these enzymes and pyrimidine-based inhibitors, researchers can develop novel therapeutic agents for treating diseases related to protein synthesis and cellular regulation.
Used in Drug Delivery Systems:
BOC-SER(BZL)-OSU can also be employed in the development of drug delivery systems, particularly for targeted drug delivery to specific cells or tissues. Its unique chemical properties allow for the design of innovative drug carriers that can improve the bioavailability and therapeutic outcomes of pyrimidine-based inhibitors.

InChI:InChI=1/C19H24N2O7/c1-19(2,3)27-18(25)20-14(12-26-11-13-7-5-4-6-8-13)17(24)28-21-15(22)9-10-16(21)23/h4-8,14H,9-12H2,1-3H3,(H,20,25)

Upstream product

• 23680-31-1 BOC-O-benzyl-L-serine 
• 90704-86-2 bis(N-hydroxysuccinimide) sulfite 
• 107960-02-1 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 

Downstream Products

• 78331-03-0 N-(t-butoxycarbonyl)-L-(O-benzyl)serinamide 
• 1239704-30-3 1-(2,4-dichlorophenyl)-N-[(1S)-2-(4-methylpiperazin-1-yl)-2-oxo-1-{[(phenylmethyl)oxy]methyl}ethyl]cyclopropanecarboxamide 
• 1239355-56-6 C₂₀H₃₁N₃O₄ 
• 1186060-32-1 C₁₇H₂₃NO₆S 
• 1257841-33-0 ethyl (S)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxopentanoate 
• 1257841-32-9 methyl (S)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxopentanoate 
• 1199558-90-1 3-benzyloxyestra-1,3,5⁽¹⁰⁾,16-tetraeno[17,16-e]-2'-(O-benzyl-N-tert-butoxycarbonyl-L-serinyl-glycyl-S-benzyl-L-cysteinylamino)pyrimidine 
• 1199559-03-9 C₅₄H₆₂N₆O₈ 

Relevant articles and documents

SYNTHESIS OF N-HYDROXYSUCCINIMIDE ESTERS OF N-PROTECTED AMINO ACIDS AND PEPTIDES USING N,N'-DISUCCINIMIDYL SULFITE

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Structure-Guided Enhancement of Selectivity of Chemical Probe Inhibitors Targeting Bacterial Seryl-tRNA Synthetase

Aminoacyl-tRNA synthetases are ubiquitous and essential enzymes for protein synthesis and also a variety of other metabolic processes, especially in bacterial species. Bacterial aminoacyl-tRNA synthetases represent attractive and validated targets for antimicrobial drug discovery if issues of prokaryotic versus eukaryotic selectivity and antibiotic resistance generation can be addressed. We have determined high-resolution X-ray crystal structures of the Escherichia coli and Staphylococcus aureus seryl-tRNA synthetases in complex with aminoacyl adenylate analogues and applied a structure-based drug discovery approach to explore and identify a series of small molecule inhibitors that selectively inhibit bacterial seryl-tRNA synthetases with greater than 2 orders of magnitude compared to their human homologue, demonstrating a route to the selective chemical inhibition of these bacterial targets.

Branched and Chain-Extended Sugars, XXXI. - Synthesis of the Deferri Form of the Oxygen Analogue of &δ1-Albomycin

The oxygen analogue of the deferri form of δ1-albomycin has been synthesized.Reaction of the xylo-dialdehyde 2 with the anion of the lithium salt 3 of N,N-bis(trimethylsilyl)glycine trimethylsilyl ester leads to the chain-extended sugar.In good stereochemical selectivity the desired 6-amino-6-desoxy-L-ido-hepturonic acid is isolated as derivative 8.After transformation of 8 into the 1-acetate 23 the nucleoside 26 is obtained by a modification of the Hilbert-Johnson reaction using the uracil derivative 24.N-Methylation of 26 gives 28 in good yield.The serine derivative 31 reacts with the deblocked amino compound 30 to yield the peptide nucleoside 32.The tripeptide 36, which contains three units of N5-acetyl-N5-hydroxyl-L-ornithine, is successfully linked to the partial deblocked compound 34 via the mixed carbonic anhydride method.Final hydrogenation of 37 gives the free deferri form of the oxygen analogue 38.