39747-65-4

Basic information

• Product Name: BOC-SER-OSU
• Synonyms: BOC-L-SERINE HYDROXYSUCCINIMIDE ESTER;BOC-L-SERINE N-HYDROXYSUCCINIMIDE ESTER;BOC-SER-OSU;BOC-L-SERINE HYDROXYSUCCINIMIDESTER;(S)-Boc-2-amino-3-hydroxypropionic acid N-hydroxysuccinimide ester;Boc-L-Ser-OSu;Boc-L-β-hydroxyalanine N-hydroxysuccinimide ester;(Tert-Butoxy)Carbonyl Ser-Osu
• CAS NO: 39747-65-4
• Molecular Formula: C₁₂H₁₈N₂O₇
• Molecular Weight: 302.28
• Mol File: 39747-65-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-SER-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-SER-OSU(39747-65-4)
• EPA Substance Registry System: BOC-SER-OSU(39747-65-4)

Safety Data

• Hazardous Substances Data: 39747-65-4(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
BOC-Ser-OSU is used as a protective group for serine amino acids to ensure the selective deprotection of the serine side chain at a later stage of peptide synthesis. This selective protection allows for the controlled assembly of peptides, preventing unwanted reactions that could compromise the integrity of the final product.
Used in Chemical Biology Research:
In the field of chemical biology, BOC-Ser-OSU is utilized for the selective modification of serine residues in proteins and peptides. This selective modification is crucial for studying the function and properties of these biomolecules, as well as for developing new therapeutic agents that target specific serine-containing sites.
Used in Medicinal Chemistry Research:
BOC-Ser-OSU plays a significant role in medicinal chemistry research, where it is employed to modify serine residues in drug candidates. This modification can enhance the pharmacological properties of the compounds, such as their stability, solubility, and binding affinity to target proteins, ultimately leading to the development of more effective therapeutic agents.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 

Downstream Products

• 1172-65-2 2-(2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 2791-03-9 2-{2-[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-3-(4-hydroxy-phenyl)-propionylamino]-3-hydroxy-propionylamino}-4-methylsulfanyl-butyric acid methyl ester 
• 2791-02-8 {1-[1-[1-(1-Hydrazinocarbonyl-3-methylsulfanyl-propylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester 
• 50903-78-1 2-(2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid 
• 1050655-22-5 Boc-Ser-(β-OH)Phe-OH 
• 1009103-05-2 C₃₂H₄₀ClN₅O₁₀S 

Relevant articles and documents

Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome

Antibiotic chloramphenicol (CHL) binds with a moderate affinity at the peptidyl transferase center of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving properties of this inhibitor, we explored ribosome binding and inhibitory activity of a number of amino acid analogs of CHL. The L-histidyl analog binds to the ribosome with the affinity exceeding that of CHL by 10 fold. Several of the newly synthesized analogs were able to inhibit protein synthesis and exhibited the mode of action that was distinct from the action of CHL. However, the inhibitory properties of the semi-synthetic CHL analogs did not correlate with their affinity and in general, the amino acid analogs of CHL were less active inhibitors of translation in comparison with the original antibiotic. The X-ray crystal structures of the Thermus thermophilus 70S ribosome in complex with three semi-synthetic analogs showed that CHL derivatives bind at the peptidyl transferase center, where the aminoacyl moiety of the tested compounds established idiosyncratic interactions with rRNA. Although still fairly inefficient inhibitors of translation, the synthesized compounds represent promising chemical scaffolds that target the peptidyl transferase center of the ribosome and potentially are suitable for further exploration.

Synthesis and radioprotective activity of new N-(amino acid)-S-acetylcysteamine and cystamine derivatives

In order to evaluate the influence of an amino acid conjugation (Sar,Ser, Phe, Pro, Thz) on S-acetylcysteamine, cystamine, N-(amino acid)-S-acetylcysteamine (14-18) and N,N'-bis (amino acid) cystamine (24-28) derivatives have been synthesized and evaluated as potential radioprotectors. Their toxicity and radioprotective activity, as the dose reduction factor (DRF) have been determined (in vivo; ip) and compared with cysteamine and cystamine parent compounds: N-glycyl-S-acetylcysteamine trifluoroacetate 1 and N,N'-bis (glycyl)cystamine bis (trifluoroacetate) 2. Among these compounds, 14 (Sar), 15 (Ser), 15a [Ser (Ac)], 16 [Phe], 24 (Sar) had significant radioprotective activity.