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

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 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 

Downstream Products

• 61533-30-0 Boc-Ser(Bzl)-Gly-OH 
• 73607-68-8 Boc-Ser(Bzl)-Leu-OH 
• 419553-35-8 {1-[2-(2-amino-ethylamino)-ethylcarbamoyl]-2-benzyloxy-ethyl}-carbamic acid tert-butyl ester 
• 1257841-32-9 methyl (S)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxopentanoate 
• 1257841-33-0 ethyl (S)-5-benzyloxy-4-tert-butoxycarbonylamino-2-methoxycarbonyl-3-oxopentanoate 
• 1186060-32-1 C₁₇H₂₃NO₆S 
• 1239704-30-3 1-(2,4-dichlorophenyl)-N-[(1S)-2-(4-methylpiperazin-1-yl)-2-oxo-1-{[(phenylmethyl)oxy]methyl}ethyl]cyclopropanecarboxamide 
• 120679-16-5 Boc-Ser(Bzl)-Ala-Hmb-Phe-ONSu 
• 1026981-10-1 {(S)-5-[(S)-2-(11-Azido-undecanoylamino)-3-benzyloxy-propionylamino]-5-phenethylcarbamoyl-pentyl}-carbamic acid benzyl ester 
• 145851-66-7 Boc-LDVPST(OBn)4 
• 145851-65-6 Boc-DVPST(OBn)4 
• 145851-63-4 Boc-VPST(OBn)3 
• 145851-64-5 Boc-PST(OBn)3 

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.

Novel Preparation of N-Protected Amino Acid Active Esters Using 1,2,2,2-Tetrachloroethyl Carbonates

1,2,2,2-Tetrachloroethyl chloroformate reacts with substituted phenols or N-hydroxy imides to yield crystalline and stable mixed aryl or oximido tetrachloroethyl carbonates.When allowed to react with an N-protected amino acid derivative, these compounds proved to be efficient for the syntheses of the corresponding active esters.A series of active esters including p-nitrophenol, trichlorophenol, pentafluorophenol, and N-hydroxysuccinimide derivatives were prepared by this new procedure.