80354-38-7

Upstream product

• 3392-05-0 Boc-Ala-O-N-hydroxysuccinimide 
• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 929681-22-1 2-oxo-2-phenylethyl-(S)-N-Boc-thioalanate 
• 1240487-37-9 Boc-Ala-Cys-red-Pro-anilide 
• 1240487-38-0 Boc-Ala-Cys-red-Tyr(OBn) anilide 
• 1240487-43-7 Boc-Ala-Cys-red-Pro-Glu(OtBu)-Phe-Asn(Trt)-Ala-OH 
• 1265278-18-9 methyl 2-(1-((S)-2-(tert-butoxycarbonylamino)-N-(2,4-dimethoxybenzyl)propanamido)-2-methylpropyl)-5-phenylthiazole-4-carboxylate 
• 1265278-15-6 tert-butyl (2S)-1-((1-(4-(benzylcarbamoyl)thiazol-2-yl)-2-methylpropyl)-(2,4-dimethoxybenzyl)amino)-1-oxopropan-2-ylcarbamate 
• 1265278-19-0 tert-butyl (2S)-1-((1-(4-(benzylcarbamoyl)-5-phenylthiazol-2-yl)-2-methylpropyl)-(2,4-dimethoxybenzyl)amino)-1-oxopropan-2-ylcarbamate 
• 51814-55-2 tert-butyl (S)-[1-(benzylamino)-1-oxopropan-2-yl]carbamate 
• 269064-59-7 (S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxopropan-2-yl)carbamate 
• 1009102-82-2 C₃₂H₃₉ClN₄O₉S₂ 
• 238748-81-7 tert-butyl N-<(1S)-2-<<1,1-dimethyl-2--2-thioxoethyl>amino>-1-methyl-2-oxoethyl>carbamate 

Relevant academic research and scientific papers

Resin-bound sulfonyl azides: Efficient loading and activation strategy for the preparation of the N-acyl sulfonamide linker

(Chemical Equation Presented) This paper describes an optimized protocol for the efficient loading of resin-bound aminoemane sulfonyl azides by either Boc- or Fmoc-protected amino thioacids. The resulting N-acyl sulfonamide is a convenient linker for use

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.

Thioacetic acid/NaSH-mediated synthesis of N -protected amino thioacids and their utility in peptide synthesis

Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.

Copper(ii) mediated facile and ultra fast peptide synthesis in methanol

A novel, ultrafast, mild and scalable amide bond formation strategy in methanol using simple thioacids and amines is described. The mechanism suggests that the coupling reactions are initially mediated by CuSO4· 5H2O and subsequently catalyzed by in situ generated copper sulfide. The pure peptides were isolated in satisfactory yields in less than 5 minutes. The Royal Society of Chemistry 2012.

T3P (propylphosphonic anhydride) mediated conversion of N α-protected amino/peptide acids into thioacids

A general, mild and an efficient protocol, which makes use of T3P as an acid activator for the synthesis of Nα-protected amino/peptide thioacids from corresponding acids in the presence of finely ground Na 2S as hydrosulfide ion donor is described. The protocol employed significantly increases the overall efficiency as the yield, reaction duration and purity of even sterically hindered amino acids.

Screening multicomponent reactions for X-linked inhibitor of apoptosis-baculoviral inhibitor of apoptosis protein repeats domain binder

We report a second example of a general reaction screening approach to discover low molecular weight inhibitors of protein protein interactions. On the basis of the known pharmacophore model of SMAC mimetics, we predicted several inhibitors based on four

Assembly/disassembly of drug conjugates using imide ligation

A strategy is described that allows the easy assembly and controlled disassembly of drug conjugates. Imide ligation, that is, the reaction of a peptide thioacid with an azidoformate, is used for conjugate assembly. The imide bond participates also with an endopeptidase-triggered cyclization-based disassembly mechanism.

Chemoselective peptidomimetic ligation using thioacid peptides and aziridine templates

Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process e

Design and synthesis of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity

A series of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA) was synthesized and their anti-HBV activity was evaluated in HepG 2 2.2.15 cells. Compounds 11, 12, 21, 22, 26, and 27 demonstrated more potent anti-HBV act

Synthesis of chiral 3,4,5,6-tetrahydro-1,4-thiazin-2-ones (thiamorpholin-2-ones) - Novel heterocycles possessing enhanced carbonyl electrophilicity over their oxygen counterparts

We report herein the first synthesis of chiral derivatives possessing the 1,4-thiazinone core. As predicted, the thiolactone is more susceptible to nucleophilic attack than the equivalent lactone system. Georg Thieme Verlag Stuttgart.