16947-86-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-BOC-3-AMINO-2-(P-TOLUENESULFONYLAMINO)-PROPIONIC ACID is used as a key building block for the synthesis of various peptides and pharmaceuticals. Its application is primarily driven by its ability to protect amino acids during the peptide synthesis process, which is crucial for the successful creation of specific peptide sequences and the development of targeted therapeutic agents.
Used in Research and Development:
In the realm of research and development, Boc-Amino-PTS is employed as an important reagent for the protection of amino acids during peptide synthesis. This protection is vital for the accurate and efficient synthesis of complex peptide structures, which are often the focus of cutting-edge research in drug discovery and development. (S)-BOC-3-AMINO-2-(P-TOLUENESULFONYLAMINO)-PROPIONIC ACID's role in safeguarding amino acids allows researchers to explore new peptide-based therapeutic strategies and advance the field of peptide chemistry.
Used in Solid-Phase Peptide Synthesis:
(S)-BOC-3-AMINO-2-(P-TOLUENESULFONYLAMINO)-PROPIONIC ACID is used as a protective agent for amino acids in solid-phase peptide synthesis. This technique is a widely utilized method for the production of peptides, where Boc-Amino-PTS ensures the selective protection of amino groups, preventing unwanted side reactions and facilitating the stepwise assembly of the desired peptide sequence. Its application in this process is essential for the efficient and reliable synthesis of peptides with specific biological activities and potential pharmaceutical applications.

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 21753-19-5 2-(S)-p-toluenesulfonylamino-β-alanine 
• 98-59-9 p-toluenesulfonyl chloride 
• 36212-66-5 N²-(toluene-4-sulfonyl)-L-asparagine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 169604-92-6 (S)-3-tert-Butoxycarbonylamino-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 77087-60-6 methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate 
• 77087-65-1 (S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester 
• 77087-64-0 methyl N-(benzyloxycarbonyl)glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoate 
• 77087-66-2 (S)-2-({(R)-1-[(S)-2-(2-Amino-acetylamino)-3-phenyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-tert-butoxycarbonylamino-propionic acid 2,4,5-trichloro-phenyl ester 
• 77100-18-6 cyclo(glycyl-L-phenylalanyl-D-prolyl-N^β-(tert-butoxycarbonyl)-L-α,β-diaminopropanoyl) 
• 58457-98-0 methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate 
• 16947-84-5 N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine 
• 96846-12-7 (S)-3-tert-Butoxycarbonylamino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-propionic acid ethyl ester 
• 96845-90-8 ethyl N²-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-N³-<(1,1-dimethylethoxy)carbonyl>-2,3-diaminopropanoate 
• 96845-97-5 N²-<4-(methylamino)benzoyl>-N^ω-<(1,1-dimethylethoxy)carbonyl>-2,ω-diaminopropanoic acid ethyl ester 
• 100484-54-6 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid 
• 199853-65-1 (S)-3-(3-methylbenzyl)amino-2-(4-toluenesulfonyl)amino-1-propanol 
• 199853-71-9 ethyl (S)-N-methyl-N-{3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propyl}aminoacetate 

Relevant academic research and scientific papers

Asymmetric synthesis of (R)-6-amino-1-methyl-4-(3-methyl- benzyl)hexahydro-1H-1,4-diazepine from L-asparagine

An efficient asymmetric synthesis of (R)-6-amino-1-methyl-4-(3- methylbenzyl)hexahydro-1H-1,4-diazepine [(R)-2] which serves as the amine part of (R)-1, a potent and selective 5-HT3 receptor antagonist, is described. Formation of the hexahydro-

Syntheses and Evaluation as Antifolates of MTX Analogues Derived from 2,ω-Diaminoalkanoic Acids

Methotrexate (MTX) analogues 27a-c bearing 2,ω-diaminoalkanoic acids (ornithine and its two lower homologues) in place of glutamic acid were synthesized by routes proceeding through N2--Nω--2,ω-diaminoalkanoic acids ethyl esters (12a,b) and N2--N5--2,5-diaminopentanoic acid (13) followed by alkylation with 6-(bromomethyl)-2,4-pteridinediamine hydrobromide.Reactions at the terminal amino group of 27-type analogues or of appropriate precursors led to other MTX derivatives whose side chains terminate in ureido (23a,b), methylureido (24), N-methyl-N-nitrosoureido (30), N-(2-chloroethyl)-N-nitrosoureido (31), and 4-chlorobenzamido (28a-c) groups.Also prepared were unsymmetrically disubstituted ureido types resulting from addition of ethyl isocyanatoacetate and diethyl 2-isocyanotoglutarate to the ethyl esters of 27a,b.Of these ureido adducts (32a,b and 33a,b, respectively), only 33a was successfully hydrolyzed to the corresponding pure acid, in this instance the tricarboxylic acid 34, a pseudo-peptide analogue of the MTX metabolite MTX-γ-Glu.Bilogical evaluations of the prepared compounds affirmed previous findings that the γ-carboxyl is not required for tight binding to dihydrofolate reductase (DHFR) but is operative in the carrier-mediated transport of classical antifolates through cell membranes.High tolerance levels observed in studies against L1210 leukemia in mice suggest the reduced potency may be due not only to lower transport efficacy but also to loss of the function of intracellular γ-polyglutamylation.The N-nitrosoureas 30 and 31 showed appreciable activity in vivo vs.L1210, but the activity did not appear to be due to antifolate action as evidenced by their poor inhibition of both L1210 DHFR and cell growth in vitro.