77167-46-5

Upstream product

• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 94580-89-9 N-benzyloxycarbonyl-L-leucine 2,4,6-trichlorophenyl ester 
• 61-90-5 L-leucine 
• 2018-66-8 Z-Leu-OH 
• 506-59-2 N,N-dimethylammonium chloride 
• 72080-89-8 N²-(tert-butoxycarbonyl)-N,N-dimethyl-L-leucinamide 
• 83892-00-6 N-benzyloxycarbonyl-L-leucine dimethylamide 

Downstream Products

• 302800-35-7 N-(2-Ethoxycarbonyl-1-cyclohexenyl)-L-leucine dimethylamide 
• 609366-95-2 (R)-2-[(Benzyloxy-formyl-amino)-methyl]-hexanoic acid ((S)-1-dimethylcarbamoyl-3-methyl-butyl)-amide 
• 233684-36-1 C₂₂H₃₅N₃O₄ 
• 1001332-87-1 Fmoc-Cys(Trt)-Leu-NMe₂ 
• 1438263-79-6 (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-(4-bromobenzyl)-N,N,4-trimethylpentan-1-ammonium bromide 
• 1438263-80-9 (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)-N-(4-bromobenzyl)-N,N,4-trimethylpentan-1-ammonium bromide 
• 1438263-81-0 (S)-N-(4-bromobenzyl)-N,N,4-trimethyl-2-(3-(4-nitrophenyl)thioureido)pentan-1-ammonium bromide 
• 1438263-89-8 C₁₇H₂₃F₆N₃S 
• 1438263-78-5 C₂₂H₃₁N₄O₂S⁽¹⁺⁾*Br^(1-) 

Relevant academic research and scientific papers

Peptidomimetics for Targeting Protein-Protein Interactions between DOT1L and MLL Oncofusion Proteins AF9 and ENL

MLL-fusion proteins, AF9 and ENL, play an essential role in the recruitment of DOT1L and the H3K79 hypermethylation of MLL target genes, which is pivotal for leukemogenesis. Blocking these interactions may represent a novel therapeutic approach for MLL-rearranged leukemia. Based on the 7 mer DOT1L peptide, a class of peptidomimetics was designed. Compound 21 with modified middle residues, achieved significantly improved binding affinities to AF9 and ENL, with KD values of 15 nM and 57 nM, respectively. Importantly, 21 recognizes and binds to the cellular AF9 protein and effectively inhibits the AF9-DOT1L interactions in cells. Modifications of the N- and C-termini of 21 resulted in 28 with 2-fold improved binding affinity to AF9 and much decreased peptidic characteristics. Our study provides a proof-of-concept for development of nonpeptidic compounds to inhibit DOT1L activity by targeting its recruitment and the interactions between DOT1L and MLL-oncofusion proteins AF9 and ENL.

Novel bifunctional thiourea-ammonium salt catalysts derived from amino acids: Application to highly enantio- and diastereoselective aza-Henry reaction

The development of new efficient and easily accessible catalysts has been one of the focuses in asymmetric phase-transfer catalysis. In this paper, a novel class of chiral bifunctional thiourea-ammonium phase-transfer catalysts were synthesized from commercially available α-amino acids. The structural modularity of these catalysts permits facile tunings to achieve optimum results, which was demonstrated in catalyzing the aza-Henry reaction with excellent enantioselectivities (up to 99.5% ee) and diastereoselectivities (up to >25:1 dr).

Ring-Opening polymerization of lactides catalyzed by natural Amino-Acid based zinc catalysts

A series of chiral NNO-tridentate Schiff base ligands derived from natural amino acids were reacted with zinc(bis-trimethylsilylamide)2 to provide metal complexes which have been fully characterized. One of these derivatives was further reacted

β-Sheet hydrogen bonding patterns in cystine peptides

Cystine peptides have been shown to adopt conformations in organic solvents that mimic small β-sheets. Relative hydrogen bond strengths, β-strand aggregation, and the identity of individual hydrogen bond donors and acceptors have been identified through h

Structure-activity relationships of the peptide deformylase inhibitor BB-3497: Modification of the P2′ and P3′ side chains

Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to both the P2′ and P3′ side chains. Enzyme inhibition and antibacterial activity data revealed that a variety of substituents are tolerated at the P2′ and P3′ positions of the inhibitor backbone. The data from this study highlights the potential for modification at the P2′ and P3′ positions to optimise the physicochemical properties.

New auxiliaries for copper-catalyzed asymmetric Michael reactions: Generation of quaternary stereocenters at room temperature

Dialkyl amides of L-valine, L-isoleucine, and L-tert-leucine (2) are excellent chiral auxiliaries for the construction of quaternary stereocenters at ambient temperature. Enaminoesters 3, prepared from these auxiliaries 2 and Michael donors 1. undergo a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone (MVK, 4) to afford products 5 in 70-90% yield and 90-99% ee (enantiomeric excess). The exclusion of moisture or oxygen is not necessary. The auxiliaries 2 are readily available by standard procedures. After workup they can be recovered almost quantitatively.

New chiral auxiliaries for the construction of quaternary stereocenters by copper-catalyzed Michael reactions

The construction of quaternary stereocenters with 95-99% ee at ambient temperatures can be achieved by a copper-catalyzed Michael reaction with the application of α-amino acid amides as chiral auxiliaries [Eq. (1)]. These amides can be obtained in a few steps from the α-amino acids with standard transformations and, after the Michael reaction, they can be quantitatively recovered. Exclusion of water and oxygen is not necessary.

A novel chiral pentamine ligand for enantioselective α-alkylation of acyclic lithium amide enolates. Optimization of chiral ligands for asymmetric reactions using solid-phase organic synthesis

(equation presented) A novel pentamine ligand has been developed for enantioselective α-alkylation of simple acyclic lithium amide enolates. It has been demonstrated that solid-phase organic synthesis provides a powerful and rapid method for finding effic

Stereochemical requirements for β-hairpin formation: Model studies with four-residue peptides and depsipeptides

Spectroscopic and crystallographic data are present for a series of tetrapeptides and analogous depsipeptides that can form a minimal β-hairpin (two intramolecular hydrogen bonds). These model compounds have been used to test the hypothesis that 'mirror image' β-turns promote β-hairpin formation. This hypothesis was inspired by a statistical survey of β-hairpins in globular proteins (Sibanda, B.L.; Thornton, J.M. Nature 1985, 316, 170), which showed that mirror image β-turns (type I' and type II'), although rare in general, are very commonly associated with β-hairpins containing a two-residue loop between the strand segments. Each of our four-residue molecules contains proline at the second position, to promote a central β-turn. The β-turn is induced to be either 'common' or 'mirror-image', relative to the outer residues, by choice of residue configuration (L vs D). In methylene chloride, end-capped tetrapeptide Ac-L-Val-D-Pro-D-Ala-L-Leu-NMe2 folds largely into the β-hairpin conformation, while the diastereomer Ac-L-Val-L-Pro-L-Ala-L-Leu-NMe2 displays little or no β-hairpin folding. For each diastereomer, the hydrogen-bonded driving force for β-hairpin folding is identical, and the dramatic difference in folding behavior therefore reflects a variation in the intrinsic conformational properties of the diastereomeric backbones. Similar behavior is seen for the diastereomeric peptide pair Ac-L-Val-D-Pro-Gly-L-Leu-NMe2 vs Ac-L-Val-L-Pro-Gly-L-Leu-NMe2, and for the analogous depsipeptides with a lactic acid or glycolic acid residue at the third position. Thus, our results show not only that mirror-image Pro-X turns strongly promote β-hairpin folding, but also that common β-turns strongly discourage formation of a β-hairpin with a two-residue loop.