17689-58-6

Upstream product

• 4299-70-1 L-tryptophan methyl ester 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 1059596-63-2 N-Cbz-L-tryptophan p-tolylthiol ester 
• 50305-28-7 Cbz-L-Tryptophan-OSu 
• 501-53-1 benzyl chloroformate 
• 73-22-3 L-Tryptophan 

Downstream Products

• 57850-17-6 (2S)-2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-(1H-indol-3-yl)propanoic acid 
• 918902-46-2 N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophanyl-(1-tert-butoxycarbonyl-L-tryptophan methyl ester) 
• 20829-55-4 (3S,6S)-3,6-Bis-(1H-indol-3-ylmethyl)-piperazine-2,5-dione 
• 82989-13-7 Z-(L)-Trp-(L)-Trp-(L)-Pro-PNP 

Relevant academic research and scientific papers

Self-assembling tryptophan-based designer peptides as intracellular delivery vehicles

A series of tryptophan-based peptides W1a, b-W4a, b, with diverse architectures were designed and synthesized. These tryptophan containing peptides can self-assemble to spherical particle. This self-assembled system was demonstrated to encapsulate rhodamine B and penetrate the cell membrane.

AgNTf2-mediated allylation with allylsilanes at C3a-position of hexahydropyrroloindoles: Application to total syntheses of amauromine alkaloids

A protocol for the allylation at the C3a-position of hexahydropyrroloindole using allylsilanes is developed. AgNTf2 proved to be an efficient activator of halopyrroloindoline substrates. This method is applicable to the introduction of various allyl group

Synergism between genome sequencing, tandem mass spectrometry and bio-inspired synthesis reveals insights into nocardioazine B biogenesis

Marine actinomycete-derived natural products continue to inspire chemical and biological investigations. Nocardioazines A and B (3 and 4), from Nocardiopsis sp. CMB-M0232, are structurally unique alkaloids featuring a 2,5-diketopiperazine (DKP) core functionalized with indole C3-prenyl as well as indole C3- and N-methyl groups. The logic of their assembly remains cryptic. Bioinformatics analyses of the Nocardiopsis sp. CMB-M0232 draft genome afforded the noz cluster, split across two regions of the genome, and encoding putative open reading frames with roles in nocardioazine biosynthesis, including cyclodipeptide synthase (CDPS), prenyltransferase, methyltransferase, and cytochrome P450 homologs. Heterologous expression of a twelve gene contig from the noz cluster in Streptomyces coelicolor resulted in accumulation of cyclo-l-Trp-l-Trp DKP (5). This experimentally connected the noz cluster to indole alkaloid natural product biosynthesis. Results from bioinformatics analyses of the noz pathway along with challenges in actinomycete genetics prompted us to use asymmetric synthesis and mass spectrometry to determine biosynthetic intermediates in the noz pathway. The structures of hypothesized biosynthetic intermediates 5 and 12-17 were firmly established through chemical synthesis. LC-MS and MS-MS comparison of these synthetic compounds with metabolites present in chemical extracts from Nocardiopsis sp. CMB-M0232 revealed which of these hypothesized intermediates were relevant in the nocardioazine biosynthetic pathway. This established the early and mid-stages of the biosynthetic pathway, demonstrating that Nocardiopsis performs indole C3-methylation prior to indole C3-normal prenylation and indole N1′-methylation in nocardioazine B assembly. These results highlight the utility of merging bioinformatics analyses, asymmetric synthetic approaches, and mass spectrometric metabolite profiling in probing natural product biosynthesis.

HMDO-promoted peptide and protein synthesis in ionic liquids

Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.

Three types of induced tryptophan optical activity compared in model dipeptides: Theory and experiment

The tryptophan (Trp) aromatic residue in chiral matrices often exhibits a large optical activity and thus provides valuable structural information. However, it can also obscure spectral contributions from other peptide parts. To better understand the indu

TREATMENT OF PROTEIN FOLDING DISORDERS

In certain embodiments, the invention is directed to a method for treating a protein folding disorder such as Alzheimer's disease, dementia, Parkinson's disease, Huntington's disease and prion-based spongiform encephalopathy. The method comprises the administration to a subject of a compound of the formula (I) wherein A and B are independently a mono- or bicyclic aromatic group or heteroaromatic cyclic group. In preferred embodiments, the compounds are bis-indole compounds.

STEREOSELECTIVITY IN MICELLAR AND VESICULAR REACTIONS

The diastereoselectivity of esterolytic cleavage of certain dipeptide and tripeptide activated esters is lower in thio-functionalized vesicles than in comparable micelles.This is thought to be a mechanism-specific effect related to the greater molecular o

Ground- and Excited-State Conformational Differences between Diastereomeric Dipeptides

Ground- and excited-state conformations of D-tryptophanyl-L-tryptophan methyl ester (1DL) L-tryptophanyl-L-tryptophan methyl ester (1LL) have been investigated by 1H NMR and by steady-state and subnanosecond time-resolved fluorescenc