70232-19-8

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-((TERT-BUTOXYCARBONYL)AMINO)-4-(DIMETHYLAMINO)-4-OXOBUTANOIC ACID is used as a coupling reagent in peptide synthesis for the production of peptides and small molecule drugs. Its ability to facilitate the formation of peptide bonds is crucial for creating complex peptide structures with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, (S)-2-((TERT-BUTOXYCARBONYL)AMINO)-4-(DIMETHYLAMINO)-4-OXOBUTANOIC ACID is utilized as a protecting group for the amine group. This function allows chemists to selectively manipulate other functional groups within a molecule without affecting the amine, which is particularly valuable in the synthesis of complex organic compounds and the development of new chemical reactions.

Upstream product

• 70232-20-1 (S)-2-tert-Butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester 
• 30925-18-9 2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 

Downstream Products

• 198956-53-5 [1-((S)-2-tert-Butoxycarbonylamino-3-dimethylcarbamoyl-propionylamino)-ethyl]-phosphonic acid diphenyl ester 
• 198956-37-5 [(S)-1-((S)-3-Benzylcarbamoyl-3,3-difluoro-2-hydroxy-1-methyl-propylcarbamoyl)-2-dimethylcarbamoyl-ethyl]-carbamic acid tert-butyl ester 
• 453509-75-6 2-tert-butoxycarbonylamino-N,N-dimethyl-succinamic acid 1-benzylcarbamoyl-2-tert-butoxycarbonylamino-propyl ester 
• 453509-76-7 N¹-(2-benzylcarbamoyl-2-hydroxy-1-methyl-ethyl)-2-[2-(3,3-dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N⁴,N⁴-dimethyl-succinamide 
• 1094531-02-8 (6S,9S,12S,15S)-methyl 12-((tert-butyldiphenylsilyloxy)methyl)-6-(2-(dimethylamino)-2-oxoethyl)-2,2,9,15-tetramethyl-4,7,10,13-tetraoxo-3-oxa-5,8,14-triazahexadecan-16-oate 
• 1028270-55-4 (S)-2-[(S)-2-(3,3-Dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N¹-[2-hydroxy-1-methyl-2-((S)-1-phenyl-ethylcarbamoyl)-ethyl]-N⁴,N⁴-dimethyl-succinamide 
• 1027169-52-3 (S)-2-[(S)-2-(3,3-Dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N¹-[2-hydroxy-1-methyl-2-((R)-1-phenyl-propylcarbamoyl)-ethyl]-N⁴,N⁴-dimethyl-succinamide 
• 1027972-80-0 (S)-N¹-[2-(2-Benzyloxy-ethylcarbamoyl)-2-hydroxy-1-methyl-ethyl]-2-[(S)-2-(3,3-dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N⁴,N⁴-dimethyl-succinamide 

Relevant academic research and scientific papers

Active-site studies of neurohypophyseal hormones: Synthesis and pharmacological properties of [5-(N4,N4-dimethylasparagine)]oxytocin

Synthesis and biological properties of [5 (N4, N4-demethylasparagine)] oxytocin are reported. In this analogue, the hydrogens of the primary carboxamide moiety in the side chain of the asparagine residue in position 5 of the posterior pituitary hormone oxytocin have been replaced by two methyl groups. The protected nonapeptide intermediate was prepared by a stepwise procedure using solution techniques. The analogue possess 4.60 ± 0.03 units/mg (mean ± SEM) uterotonic activity on the isolated rat uterine horn and 9.14 ± 0.03 units/mg of avian vasodepressor activity. Moreover, it displays an identical intrinsic activity in the in vitro rat uterotonic assay as oxytocin, when tested in the presence of either 0.5 mM Ca2+ (standard assay conditions) or at reduced levels of Ca2+ (0.3, 0.15, and 0.05 mM). This result is significant in view of the proposed biologically active model of oxytocin, in which the side chain of the 5 position residue was assigned to contain an 'active element' responsible for the intrinsic activity of the hormone when bound to the uterine receptor.

Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes

Extension of the previously reported modification of Passerini multicomponent reaction (involving condensation with N-Boc-α-aminoaldehydes followed by a deprotection-transacylation step) to α-aminoacid derived carboxylic or isocyanide components, allowed the highly convergent and short synthesis of complex peptidomimetic structures, including known potent inhibitors of serine proteases.