27317-69-7

Usage

Uses

Used in Pharmaceutical Industry:
BOC-ALA-ALA-OH is utilized as a building block in peptide synthesis for the creation of extended peptide chains. Its protective BOC group ensures the controlled formation of peptide bonds, which is crucial for the development of therapeutic peptides with specific biological activities.
Used in Research Applications:
In research settings, BOC-ALA-ALA-OH serves as a fundamental component in the synthesis of peptides for studying their structure, function, and interactions with biological systems. Its stable nature and ease of manipulation make it an ideal candidate for experimental procedures in peptide chemistry.
Used in Industrial Applications:
BOC-ALA-ALA-OH is employed in the industrial production of peptides for various commercial uses, such as in the development of pharmaceuticals, diagnostics, and other biotechnological products. Its predictable reactivity and protective BOC group facilitate the large-scale synthesis of peptides with high purity and consistency.

InChI:InChI=1/C11H20N2O5/c1-6(8(14)12-7(2)9(15)16)13-10(17)18-11(3,4)5/h6-7H,1-5H3,(H,12,14)(H,13,17)(H,15,16)

Upstream product

• 1948-31-8 di-L-alanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-38-3 L-N-Boc-Ala 
• 1115-59-9 (S)-alanine ethyl ester hydrochloride 
• 1464-43-3 seleno-L-cystine 
• 1146929-22-7 (S)-O-(tert-butyl) N-(thietan-2-on-3-yl) carbamate 
• 56-41-7 L-alanin 
• 2483-49-0 tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester 
• 83904-90-9 Boc-Ala-N-hydroxysuccinimide ester 
• 1280225-71-9 C₁₈H₂₈N₂O₆ 
• 73488-76-3 N-t-butyloxycarbonyl-alanine-N'-hydroxysuccinimide ester 
• 18670-98-9 N-(tert-butoxycarbonyl)-L-alanyl-L-alanine benzyl ester 
• 19794-10-6 (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 

Downstream Products

• 160140-78-3 5-((L-((tert-butyloxycarbonyl)amino)alanyl-L-alanyl)amino)-4-hydroxy-6-phenylhexanoic acid benzhydrylamide 
• 1053635-49-6 {(S)-1-[(S)-1-((1S,2S)-4-{[(1H-Benzoimidazol-2-yl)-phenyl-methyl]-carbamoyl}-1-benzyl-2-hydroxy-butylcarbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 1948-31-8 di-L-alanine 
• 102838-97-1 (S)-S-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-74-1 (S)-S-(4-fluorophenyl) 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-73-0 (S)-S-(3-chlorophenyl) 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-72-9 (S)-S-(2-chlorophenyl) 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-71-8 (S)-S-(4-chlorophenyl) 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-70-7 (S)-S-(4-methoxyphenyl) 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-69-4 (S)-S-phenyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-68-3 (S)-S-(4-nitrophenyl) 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanethioate 
• 1620161-80-9 (S)-perfluorophenyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 
• 1620161-79-6 (S)-4-methoxyphenyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 
• 201289-18-1 (S)-4-nitrophenyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 

Relevant academic research and scientific papers

Synthesis of Peptidoglycan Fragments from Enterococcus faecalis with Fmoc-Strategy for Glycan Elongation

Peptidoglycan (PGN) is an essential structural component of the bacterial cell wall conferring cell shape, which can be recognized by host-recognition proteins and receptors as well as bacterial surface proteins. In this work, the PGN partial structures from Enterococcus faecalis that contain a tetrasaccharide and an octasaccharide with a unique heptapeptide were synthesized via an Fmoc-strategy for elongation of the glycan chains. Namely, a 4′-O-Fmoc-protected disaccharide was utilized as the key intermediate in this efficient synthetic pathway for preparing various PGN fragments. Both the tetrasaccharide and octasaccharide with the unique heptapeptide were successfully synthesized for the first time.

The Role of N-Methyl Squaramides in a Hydrogen-Bonding Strategy to Fold Peptidomimetic Compounds

Small peptides and peptomimetic compounds are valuable tools to probe and study biological systems. Small synthetic peptide analogues adopt a given secondary structure driven by structural modules that organize the compound architecture. Among them, β- an

ANTI-HUMAN VISTA ANTIBODIES AND USE THEREOF

The invention provides anti-VISTA antibody drug conjugates which may be used for targeted delivery of anti-inflammatory agents such as steroids to immune cells, e.g., myeloid cells. The invention also provides methods of using anti-VISTA antibody drug conjugates in the treatment of inflammatory and/or autoimmune conditions and/or for alleviating the toxicity of anti-inflammatory agents such as steroids.

Phosphonopeptides revisited, in an era of increasing antimicrobial resistance

Given the increase in resistance to antibacterial agents, there is an urgent need for the development of new agents with novel modes of action. As an interim solution, it is also prudent to reinvestigate old or abandoned antibacterial compounds to assess

The effect of monosaccharides on self-assembly of benzenetricarboxamides

The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide derivatives aggregate into different ordered structures. When alanine linkers are introduced to these molecules between the core and the monosacchride, morphologies of three types of monosaccharide BTAs turned to disordered, meanwhile their structures become similar with the increase of the length of alanine linkers, indicating the disappearance of the monosaccharide effects.

Tripeptide based super-organogelators: Structure and function

A novel series of tripeptide-based low molecular weight super-organogelators were synthesized and characterized. Four tripeptides with diverse steric crowding at the central amino acid residue were studied. From this series, only sterically less hindered

Bicomponent β-sheet assembly of dipeptide fluorophores of opposite polarity and sensitive detection of nitro-explosives

Fluorescent hydrogels of two dipeptide-pyrene amphiphiles of opposite polarity are developed via bicomponent antiparallel β-sheet co-assembly. The helical molecular assembly resulted in the formation of fluorescent nanofibers. The sandwich-like interaction of nitroaromatics within the hydrogel matrix enabled selective and sensitive detection of toxic nitro-explosives.

Coupling of sterically demanding peptides by β-thiolactone-mediated native chemical ligation

The ligation of sterically demanding peptidyl sites such as those involving Val-Val and Val-Pro linkages has proven to be extremely challenging with conventional NCL methods that rely on exogenous thiol additives. Herein, we report an efficient β-thiolactone-mediated additive-free NCL protocol that enables the establishment of these connections in good yield. The rapid NCL was followed by in situ desulfurization. Reaction rates between β-thiolactones and conventional thioesters towards NCL were also investigated, and direct aminolysis was ruled out as a possible pathway. Finally, the potent cytotoxic cyclic-peptide axinastatin 1 has been prepared using the developed methodology.

Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated α-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4- dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-l-Orn(Boc)-Val-OMe, Fmoc-l-Cys(trt)-Gly-OEt and Boc-l-Tyr-Gly-OEt is presented.

Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups

A simple and efficient method for the chemoselective N-Boc protection of the amine moiety in a variety of compounds is described using di-tert-butyl dicarbonate and guanidine hydrochloride as an organocatalyst in ethanol at 35-40°C. Selective mono-N-Boc protection of diamines and chemoselective protection of hydroxylamines without formation of any side products is achieved. Amino acids and peptides are N-Boc protected efficiently in excellent yields under convenient reaction conditions.