268553-44-2

Upstream product

• 78981-25-6 N-(tert-butoxycarbonyl)-D-alanine amide 
• 91103-47-8 N-(tert-butoxycarbonyl)-D-alanine methyl ester 
• 3744-87-4 Boc-(R)-Ala 

Downstream Products

• 406938-58-7 N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt 

Relevant academic research and scientific papers

ANTIBACTERIAL COMPOUNDS

Novel compounds having antimicrobial activitiy, in particular against Pseudomonas aeruginosa, Burkholderia cepaciaand/or Clostridium difficile, and a pharmaceutical composition containing the novel compound.

Painting argyrins blue: Negishi cross-coupling for synthesis of deep-blue tryptophan analogue β-(1-azulenyl)-L alanine and its incorporation into argyrin C

The argyrins are a family of non-ribosomal peptides that exhibits different biological activities through only small structural changes. Ideally, a biologically active molecule can be tracked and observed in a variety of biological and clinical settings in a non-invasive manner. As a step towards this goal, we report here a chemical synthesis of unnatural deep blue amino acid β-(1-azulenyl)-L alanine with different fluorescence and photophysical properties, which allows a spectral separation from the native tryptophan signal. This might be especially useful for cell localization studies and visualizing the targeted proteins. In particular, the synthesis of β-(1-azulenyl)-L alanine was achieved through a Negishi coupling which proved to be a powerful tool for the synthesis of unnatural tryptophan analogs. Upon β-(1-azulenyl)-L alanine incorporation into argyrin C, deep blue octapeptide variant was spectrally and structurally characterized.

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.

Design, synthesis and anticancer mechanistic studies of linked azoles

Herein we report the synthesis and biological activity evaluation of 2,4 linked azole-containing molecules. A total of 13 linked thiazole- and oxazole-containing compounds were synthesized in good yields. Cytotoxicity evaluation of those compounds showed

OXADIAZOLE COMPOUNDS WHICH INHIBIT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF

The invention provides novel beta-secretase inhibitors and methods for their including methods of treating Alzheimer's disease.

Total synthesis of argyrins A and e

The total synthesis of argyrins A and E were accomplished using a convergent strategy by condensation of one tripeptide and two dipeptide fragments. The synthesis strategy, which was developed for the protection of peptide fragments and identification of the optimum macrocylization site, can be applied to further synthetic studies involving other members of the argyrin family.

Synthesis of the thiazole-thiazoline fragment of largazole analogues

The thiazole - thiazoline fragment of the marine natural product largazole, a potent histone deacetylase 1 inhibitor, has been synthesized in five steps. The methodology provides rapid access to thiazole-4-carbonitrile, thiazole-4-carbimidate, thiazole -

PYRIDINONYL PDK1 INHIBITORS

The present invention provides pyridinonyl PDKl inhibitors and methods of treating cancer using the same.

Dendroamide A, nostocyclamide and related cyclopeptides from cyanobacteria. Total synthesis, together with organised and metal-templated assembly from oxazole and thiazole-based amino acids

Oxazole and thiazole-based amino acids (15-18) are shown to undergo organised and metal-templated assemblies leading to novel cyclic peptides. Thus, a 1:1:1 mixture of the amino acids (15, 16 and 17) undergo cyclisation in the presence of FDPP producing t