3392-05-0

Basic information

• Product Name: Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
• Synonyms: BOC-D-ALA-OSU;BOC-D-ALANINE-OSU;BOC-D-ALANINE N-HYDROXYSUCCINIMIDE ESTER;BOC-D-ALANINE-HYDROXYSUCCINIMIDE ESTER;N-ALPHA-T-BOC-D-ALANINE N-HYDROXYSUCCINIMIDE ESTER;succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate;Boc-L-Alanine N-hydroxysuccinimde ester;BOC-L-ALA-OSU
• CAS NO: 3392-05-0
• Molecular Formula: C₁₂H₁₈N₂O₆
• Molecular Weight: 286.28
• EINECS: 222-229-7
• Product Categories: Amino Acid Derivatives;Amino Acids;Alanine [Ala, A];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 3392-05-0.mol
• Article Data: 31

Chemical Properties

• Melting Point: 161-163 °C
• Appearance: /
• Density: 1.27 g/cm³
• Refractive Index: 1.51
• Storage Temp.: −20°C
• PKA: 10.81±0.46(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 3560476
• CAS DataBase Reference: Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate(3392-05-0)
• EPA Substance Registry System: Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate(3392-05-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 3392-05-0(Hazardous Substances Data)

Usage

Description

Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is a white powder chemical compound that serves as a versatile building block in the synthesis of various biologically active molecules. Its unique structure allows it to be used in the creation of different types of compounds, making it a valuable asset in the field of organic chemistry and pharmaceutical research.

Uses

Used in Pharmaceutical Industry:
Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is used as a reactant for the synthesis of various pharmaceutical compounds, such as Muramyldipeptide analogs, Microcin C analogs, and N-Protected dipeptide acids. These analogs and derivatives have potential applications in the development of new drugs and therapies.
Used in Antibacterial Applications:
In the field of antibacterial research, Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is used as a reactant for the synthesis of Microcin C analogs. These analogs exhibit antibacterial properties, making them valuable in the development of new antibiotics to combat drug-resistant bacteria.
Used in Peptide Synthesis:
Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is used as a reactant in the synthesis of lipid I and nucleoside diphosphate peptide derivatives. These derivatives are essential in the study of peptide synthesis and have potential applications in the development of new peptide-based drugs.
Used in Cell Biology Research:
Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is used in the preparation of free and peptide-bound glycated amino acids. These glycated amino acids are crucial for studying their interactions with human Caco-2 intestinal epithelial cell apical membrane transport proteins, which can provide insights into the mechanisms of cellular transport and the development of new therapeutic strategies.
Used in Cancer Research:
In the field of cancer research, Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is used as a reactant for the synthesis of 7-Substituted camptothecin conjugates with RGD-peptides. These conjugates serve as avβ3 integrin ligands, which can be used to target specific cancer cells, potentially improving the efficacy of cancer treatments.
Used in Organic Chemistry:
Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate is used as a versatile building block in organic chemistry, allowing researchers to synthesize a wide range of compounds with various applications in different industries, including pharmaceuticals, materials science, and biotechnology.

InChI:InChI=1/C12H18N2O6/c1-7(13-11(18)19-12(2,3)4)10(17)20-14-8(15)5-6-9(14)16/h7H,5-6H2,1-4H3,(H,13,18)

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 15761-38-3 L-N-Boc-Ala 
• 75513-55-2 N-hydroxysuccinimido diphenyl phosphate 
• 107960-02-1 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate 
• 90704-86-2 bis(N-hydroxysuccinimide) sulfite 
• 16948-17-7 Boc-Ala-OH*DCHA 
• 3744-87-4 Boc-(R)-Ala 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 77422-40-3 tert-butyloxycarbonylalanyl-4-pyridylmethylester 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 23632-78-2 N-tert-butyloxycarbonyl-L-alanyl-glycine benzyl ester 
• 57177-77-2 Boc-Ala-Lys(Boc)-NHNH-Z 
• 2448-58-0 (S)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylpropanoic acid 
• 98919-97-2 (2S,6S)-2-Amino-6-((S)-2-tert-butoxycarbonylamino-propionylamino)-heptanedioic acid 
• 142811-55-0 ((S)-1-{3,5-Bis-[((S)-2-tert-butoxycarbonylamino-propionylamino)-methyl]-benzylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester 
• 114856-02-9 Boc-Ala-Lys(Z)-OBzl 
• 56618-30-5 N-(tert-butoxycarbonyl)-L-alanyl-L-leucine benzyl ester 
• 19794-10-6 (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 
• 129121-69-3 [(S)-1-(4-{Benzyloxycarbonyl-[2-(5-{2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-amino}-butylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 73870-83-4 Boc-Ala-Gly-Gly-OBzl 
• 59524-71-9 t-butoxycarbonyl-L-alanyl-L-glutamic acid dibenzyl ester 
• 18814-49-8 tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester 
• 18671-06-2 N-t-butoxycarbonyl-L-alanyl-L-alanyl-L-alanine benzyl ester 
• 114117-77-0 Boc-Ala-Lys(Z)-Lys(Z)-OPac 

Relevant articles and documents

Biodegradable microspheres VI: Lysosomal release of covalently bound antiparasitic drugs from starch microparticles

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Synthesis of pyrimidine nucleoside and amino acid conjugates

The synthesis of novel pyrimidine nucleoside bioconjugates with amino acids is presented. The N4-amino acid-acylated 2′-deoxycytidine analogues, modified with various amino acids, were synthesized using a three-step synthesis and obtained in moderate overall yields. Novel amino acid-alkylated 2′-deoxycytidine derivatives were obtained during the rearrangement of amino acid-acylated derivatives that occurred during Boc deprotection.

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.

N,O-Bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis

A method using N,O-bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) as coupling agents for dipeptide synthesis is descried. The coupling reaction between N-hydroxysuccinimide (NHS) esters and amines could be performed under mild conditions with N,O-bis(trimethylsilyl)acetamide (BSA) as coupling reagent and no additional acid/base is required. All byproducts and excessive reactants are water soluble or hydrolysable and easy to eliminate through water-washing at the purification stage. Moreover, all the reactants are inexpensive and widely used in conventional drug production.