56612-25-0Relevant academic research and scientific papers
A Comprehensive Landscape for Fibril Association Behaviors Encoded Synergistically by Saccharides and Peptides
Liu, Rongying,Zhang, Ran,Li, Long,Kochovski, Zdravko,Yao, Lintong,Nieh, Mu-Ping,Lu, Yan,Shi, Tongfei,Chen, Guosong
supporting information, p. 6622 - 6633 (2021/05/29)
Nature provides us a panorama of fibrils with tremendous structural polymorphism from molecular building blocks to hierarchical association behaviors. Despite recent achievements in creating artificial systems with individual building blocks through self-
Controlling Amphiphilic Polymer Folding beyond the Primary Structure with Protein-Mimetic Di(Phenylalanine)
Dykeman-Bermingham, Peter A.,Knight, Abigail S.,Warren, Jacqueline L.
supporting information, p. 13228 - 13234 (2021/09/03)
While methods for polymer synthesis have proliferated, their functionality pales in comparison to natural biopolymers-strategies are limited for building the intricate network of noncovalent interactions necessary to elicit complex, protein-like functions
Tricomponent Supramolecular Multiblock Copolymers with Tunable Composition via Sequential Seeded Growth
Agasti, Sarit S.,Das, Angshuman,George, Subi J.,Sarkar, Aritra,Sasmal, Ranjan,Venugopal, Akhil
supporting information, p. 18209 - 18216 (2021/07/10)
Synthesis of supramolecular block co-polymers (BCP) with small monomers and predictive sequence requires elegant molecular design and synthetic strategies. Herein we report the unparalleled synthesis of tri-component supramolecular BCPs with tunable microstructure by a kinetically controlled sequential seeded supramolecular polymerization of fluorescent π-conjugated monomers. Core-substituted naphthalene diimide (cNDI) derivatives with different core substitutions and appended with β-sheet forming peptide side chains provide perfect monomer design with spectral complementarity, pathway complexity and minimal structural mismatch to synthesize and characterize the multi-component BCPs. The distinct fluorescent nature of various cNDI monomers aids the spectroscopic probing of the seeded growth process and the microscopic visualization of resultant supramolecular BCPs using Structured Illumination Microscopy (SIM). Kinetically controlled sequential seeded supramolecular polymerization presented here is reminiscent of the multi-step synthesis of covalent BCPs via living chain polymerization. These findings provide a promising platform for constructing unique functional organic heterostructures for various optoelectronic and catalytic applications.
Transition-metal ion-mediated morphological transformation of pyridine-based peptide nanostructures
Singh, Narendra,Singh, Ramesh,Sharma, Swati,Kesharwani, Khushboo,Joshi, Khashti Ballabh,Verma, Sandeep
supporting information, p. 153 - 161 (2021/01/11)
Inspired by natural metallopeptides, we have rationally designed two pyridine-conjugated short peptides. These two peptide conjugates formed a pair of constitutional isomers that helped us describe their structure-function relationship. Both the isomers consisted of an equal number of aromatic amino acid residues, but shuffling was observed in the position of two key amino acids, viz; tyrosine and phenylalanine, which brought a remarkable change in their self-assembling behavior. The presence of specific functional groups and chemical diversity in both conjugates made them very active towards metal coordination. Both the constitutional isomers adopted different pathways of self-assembly, which could be further controlled or transformed by the use of transition metal ions. Interestingly, it was observed that the metal ions could precisely control the morphology of these metallopeptide nanostructures and make them more stable. Therefore, such artificial metallopeptides possess remarkable advantages over the natural counterparts primarily due to their tailor-made chemical structures.
Silica covering driven intensity enhancement and handedness inversion of the CPL signals of the supramolecular assemblies
Jiang, Pan,Li, Hongkun,Liu, Wei,Li, Yi,Li, Baozong,Yang, Yonggang
, p. 8986 - 8992 (2021/06/06)
A pair of Phe-Phe dipeptides with a tolane group were synthesized by introducing tolane with high emission efficiency to phenylalanine dipeptide. The sodium salts of the dipeptides were able to self-assemble into straight belts in a mixture of methanol and water. The supramolecular assemblies exhibited circularly polarized luminescence (CPL) properties. They can be used as templates to prepare dipeptide-based hybrid silicas through a supramolecular templating approach. The hybrid materials formed coiled nanoribbons, which showed a distinct and different morphology compared to supramolecular assemblies. Moreover, since silica covering can affect the packing structures of the tolane groups, the intensity of the CPL was enhanced and its handedness was inversed. This journal is
Unique crystallographic signatures of Boc-Gly-Phe-Phe-OMe and Boc-Gly-Phg-Phe-OMe and their self-association
Giri, Rajat Subhra,Mandal, Bhubaneswar
, p. 236 - 243 (2019/01/10)
The self-assembly of N- and C-protected tripeptides, Boc-Gly-Phe-Phe-OMe (1) and its analog Boc-Gly-Phg-Phe-OMe (2, Phg = phenylglycine), has been investigated. The presence of just an extra methylene (-CH2-) group in the side chain of one of the amino acids resulted in significant changes in their molecular arrangement and supramolecular structure. The single crystal X-ray diffraction analysis suggested that 1 adopted a type II β-turn-like conformation, known as open turn identified by the absence of any intramolecular hydrogen bond, which further self-assembled to form a herringbone helix-like architecture through non-covalent interactions. To the best of our knowledge, this is the first report on a designed open turn tripeptide without a kink-forming element. However, in spite of the presence of a non-standard amino acid 2 adopted a β-sheet conformation which further self-organized to form a helical architecture through non-covalent interactions in the crystalline form. The conformations of these peptides in solution were also investigated by solvent dependent NMR titration, 2D NOESY, and CD spectroscopic experiments. These peptides exhibited two different flower-like architectures in acetonitrile-water medium under an optical microscope and a field emission scanning electron microscope (FESEM).
Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides
Bag, Subhendu Sekhar,De, Suranjan
supporting information, p. 1404 - 1409 (2018/03/23)
The solvatochromic IR responsivity of small side chain –NCS in two unexplored unnatural amino acids, isothiocyanyl alanine (NCSAla = Ita) and lysine (NCSLys = Itl), without perturbing the conformation is demonstrated in two designed
Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes
Xin, Bo-Tao,De Bruin, Gerjan,Huber, Eva M.,Besse, Andrej,Florea, Bogdan I.,Filippov, Dmitri V.,Van Der Marel, Gijsbert A.,Kisselev, Alexei F.,Van Der Stelt, Mario,Driessen, Christoph,Groll, Michael,Overkleeft, Herman S.
supporting information, p. 7177 - 7187 (2016/08/24)
This work reports the development of highly potent and selective inhibitors of the β5c catalytic activity of human constitutive proteasomes. The work describes the design principles, large hydrophobic P3 residue and small hydrophobic P1 residue, that led to the synthesis of a panel of peptide epoxyketones; their evaluation and the selection of the most promising compounds for further analyses. Structure-activity relationships detail how in a logical order the β1c/i, β2c/i, and β5i activities became resistant to inhibition as compounds were diversified stepwise. The most effective compounds were obtained as a mixture of cis- and trans-biscyclohexyl isomers, and enantioselective synthesis resolved this issue. Studies on yeast proteasome structures complexed with some of the compounds provide a rationale for the potency and specificity. Substitution of the N-terminus in the most potent compound for a more soluble equivalent led to a cell-permeable molecule that selectively and efficiently blocks β5c in cells expressing both constitutive proteasomes and immunoproteasomes.
Hybrid peptides endomophin-2/DAMGO: Design, synthesis and biological evaluation
Mollica, Adriano,Costante, Roberto,Stefanucci, Azzurra,Pinnen, Francesco,Luisi, Grazia,Pieretti, Stefano,Borsodi, Anna,Bojnik, Engin,Benyhe, Sándor
, p. 167 - 177 (2013/10/01)
Endomorphin-2 [Tyr-Pro-Phe-Phe-NH2] and DAMGO [Tyr-D-Ala-Gly-(N-Me)Phe-Gly-ol] are natural (EM2) and synthetic (DAMGO) opioid peptides both selective for μ opioid receptor with high analgesic activity. In this work we report synthesis, in vitro and in vivo biological evaluation of five new hybrid EM2/DAMGO analogues, with the aim to obtain compounds with high affinity at μ-opioid receptor, high activity in animal nociception tests (hot plate and tail flick) and improved enzymatic stability. Double N-methylation on both Phe residues and C-terminal ethanolamide led to analogue 6e, which possesses a good in vitro μ affinity (Kiμ = 34 nM), combined with a remarkable in vivo antinociceptive activity.
The cis-4-amino-l-proline residue as a scaffold for the synthesis of cyclic and linear endomorphin-2 analogues
Mollica, Adriano,Pinnen, Francesco,Stefanucci, Azzurra,Feliciani, Federica,Campestre, Cristina,Mannina, Luisa,Sobolev, Anatoly P.,Lucente, Gino,Davis, Peg,Lai, Josephine,Ma, Shou-Wu,Porreca, Frank,Hruby, Victor J.
experimental part, p. 3027 - 3035 (2012/06/15)
Endomorphin-2 (EM-2: Tyr-Pro-Phe-Phe-NH2) is an endogenous tetrapeptide that combines potency and efficacy with high affinity and selectivity toward the μ opioid receptor, the most responsible for analgesic effects in the central nervous system
