Article
Chemistry, Applied
Monika Kijewska, Michalina Zawadzka, Miko Laj, Piotr Stefanowicz
Summary: This study presents a fast, simple, and efficient method for the synthesis of lactosylated peptides using microwave-assisted synthesis and boronate affinity chromatography. The researchers successfully synthesized modified peptides from β-lactoglobulin and applied the functionalized resin for enrichment of lactosylated peptides in human serum albumin samples.
Article
Chemistry, Multidisciplinary
Jan Pawlas, Jon H. Rasmussen
Summary: This study demonstrates the feasibility of using Fmoc/t-Bu solid-phase peptide synthesis under aqueous conditions, utilizing a resin and solvent combination to improve resin swelling and solubility of starting materials. By developing a waste recycling method, the reuse of waste was achieved, reducing the amount of starting materials used and replacing hazardous solvents with an aqueous medium.
Article
Polymer Science
Damilola C. Akintayo, Beatriz G. de la Torre, Yongfu Li, Fernando Albericio
Summary: Amino-Li-resin is a novel polyacrylamide resin in fiber form, suitable for solid-phase peptide chemistry. It swells well in polar solvents, compatible with some non-polar solvents, and has high functional amino group loading for maximum peptide productivity. It exhibits excellent stability in both basic and acidic reagents, making it broadly applicable for biomolecule synthesis.
Article
Pharmacology & Pharmacy
Giovanni Vivenzio, Maria Carmina Scala, Pasquale Marino, Michele Manfra, Pietro Campiglia, Marina Sala
Summary: In recent years, peptides have become more successful as therapeutic compounds. The preferred method for obtaining peptides, solid-phase peptide synthesis (SPPS), does not follow the principles of green chemistry due to the use of toxic reagents and solvents. This study aimed to find an environmentally sustainable solvent to replace DMF in Fmoc SPPS. Dipropyleneglycol dimethylether (DMM), a green solvent with low toxicity and biodegradability, was tested for its applicability in various steps of SPPS. It was found that DMM is a valuable alternative to DMF in all steps of solid-phase peptide synthesis.
Review
Chemistry, Organic
Aizhan Abdildinova, Mark J. Kurth, Young-Dae Gong
Summary: Peptidomimetics are compounds with promising pharmacological properties that overcome limitations of peptides through backbone modifications. Accessible synthetic methodologies play a key role in peptidomimetic progress, with solid-phase organic synthesis serving as a powerful tool for their preparation. Numerous strategies for peptide backbone modifications via solid-phase synthesis have been developed in the last two decades.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yongwei Zhao, Edward Marschall, Maxine Treisman, Alasdair McKay, Leo Padva, Max Crusemann, David R. Nelson, David L. Steer, Ralf B. Schittenhelm, Julien Tailhades, Max J. Cryle
Summary: This study investigates the use of peptide crosslinking cytochrome P450 enzymes in generating cyclic tripeptides from simple synthons. The enzymes produced both tyrosine-histidine and tyrosine-tryptophan crosslinked tripeptides, the latter being a rare example of phenolic crosslinking to an indole moiety. The tripeptides can be easily isolated after removing the leader peptide and can include a wide range of amino acids. This research suggests that P450 enzymes have the potential to play a significant role in the synthesis of high-value cyclic tripeptides, which can be further diversified using selective chemical techniques.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tingting Cui, Junyou Chen, Rui Zhao, Yanyan Guo, Jiahui Tang, Yulei Li, Yi-Ming Li, Donald Bierer, Lei Liu
Summary: The synthesis of an Asp lactam derivative of A-183, a selective inhibitor of Factor 7a with good anticoagulant and antithrombotic activity, was achieved by using a removable backbone modification (RBM) strategy. This strategy was also successfully applied to the synthesis of a second Asp lactam derivative, demonstrating its potential as a general method for synthesizing Asp lactam cyclic peptides.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yue Wu, Ho-Fai Chau, Waygen Thor, Kaitlin Hao Yi Chan, Xia Ma, Wai-Lun Chan, Nicholas J. Long, Ka-Leung Wong
Summary: A new synthetic protocol for multifunctional fluorescent cyclopeptides was introduced, allowing for the creation of various bicyclic peptides and the transformation of embedded dipyrrin into fluorescent BODIPY or a metal sensor. This provides a valuable addition to the peptide macrocyclization toolbox and a blueprint for developing multifunctional dipyrrin linkers in cyclopeptides for a range of potential bioapplications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Vladimir Khatskelevich Khavinson, Irina Grigor'evna Popovich, Natalia Sergeevna Linkova, Ekaterina Sergeevna Mironova, Anastasiia Romanovna Ilina
Summary: Peptides have a wide range of biological activity, regulating functions of the endocrine, nervous, and immune systems through gene expression and protein synthesis. Short peptides can interact with cell nuclei and DNA structures, participating in important processes such as gene transcription, replication, and repair, as well as regulating DNA methylation status. They may have been among the earliest signaling molecules in evolution.
Article
Biochemistry & Molecular Biology
Urszula Bachor, Agnieszka Lizak, Remigiusz Bachor, Marcin Maczynski
Summary: Hybrid peptides composed of alpha and beta-amino acids have potential as therapeutic agents. Therefore, the development of new unnatural amino acids and methods for their incorporation is important. In this study, we investigated the application of 5-amino-3-methyl-isoxazole-4-carboxylic acid (AMIA) in solid phase peptide synthesis. The results show that this unnatural beta-amino acid can be used in synthesizing a new class of bioactive peptides.
Article
Chemistry, Multidisciplinary
Katarzyna Wegner, Danielle Barnes, Kim Manzor, Agnieszka Jardine, Declan Moran
Summary: The study aimed to find a greener solvent alternative to replace DMF in SPPS manufacturing processes at Ipsen. Greener solvents with efficient resin swelling and solubility were selected as candidates for SPPS trials in the small-scale synthesis of commercial and developmental peptides.
GREEN CHEMISTRY LETTERS AND REVIEWS
(2021)
Article
Chemistry, Organic
Srinivasa Rao Manne, Omar Luna, Gerardo A. Acosta, Miriam Royo, Ayman El-Faham, Gyorgy Orosz, Beatriz G. de la Torre, Fernando Albericio
Summary: The reaction of DIC with OxymaPure to form an oxadiazole compound and HCN is not universal among all carbodiimides, but is dependent on the alkyl structure flanking the N atoms of the carbodiimide. Two exceptions, TBEC and EDC·HCl, have been identified for their exemption from HCN formation during reaction with OxymaPure.
Article
Biochemistry & Molecular Biology
Ramakotaiah Mulamreddy, William D. Lubell
Summary: This paper reports the synthesis of 5- and 7-hydroxy indolizidin-2-one N-(Boc)amino acids from L-serine, and discusses their potential in peptide mimicry.
Article
Chemistry, Organic
Pablo Tovillas, Claudio D. Navo, Paula Oroz, Alberto Avenoza, Francisco Corzana, Maria M. Zurbano, Gonzalo Jimenez-Oses, Jesus H. Busto, Jesus Peregrina
Summary: Chiral bicyclic N,O-acetal isoserine derivatives have been synthesized using acid-catalyzed reactions, which have significant applications in peptidomimetic and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shasha Chen, Dingnian Gou, Zhengkun Liu, Zhonghua Zhang, Lanxia Zhou, Shouliang Dong
Summary: DAMGO, a high-efficacy mu-opioid receptor agonist, is widely used in preclinical analgesia studies as a tool compound. Due to the large amount and high cost of DAMGO required, a simple and efficient solid-phase synthesis method was developed.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
N. D. Prasad Atmuri, William D. Lubell
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Amit Mahindra, Omar Janha, Kopano Mapesa, Ana Sanchez-Azqueta, Mahmood M. Alam, Alfred Amambua-Ngwa, Davis C. Nwakanma, Andrew B. Tobin, Andrew G. Jamieson
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Organic
Yousra Hamdane, Pradeep S. Chauhan, Suresh Vutla, Mukandila Mulumba, Huy Ong, William D. Lubell
Summary: Fifteen N-aminoimidazolone (Nai) dipeptides with different 5-position side-chain groups were synthesized through regioselective proline-catalyzed reactions and acid-mediated dehydration. Introducing 5-aryl-Nai dipeptides into CD36 receptor peptide ligands provided insights into the conformation responsible for binding affinity and anti-inflammatory activity.
Article
Cell Biology
Marie-France Dorion, Mukandila Mulumba, Shuya Kasai, Ken Itoh, William D. Lubell, Huy Ong
Summary: This study reveals that the CD36 ligand MPE-001 protects RPE cells from oxidative stress by promoting autophagy. MPE-001 reduced oxidative stress and cell apoptosis induced by NaIO3, restored autophagic flux, and this protective effect was associated with an increase in mature autophagosomes.
OXIDATIVE MEDICINE AND CELLULAR LONGEVITY
(2021)
Article
Chemistry, Medicinal
Ragnhild G. Ohm, Mukandila Mulumba, Ramesh M. Chingle, Ahsanullah, Jinqiang Zhang, Sylvain Chemtob, Huy Ong, William D. Lubell
Summary: Expanding cyclic peptide diversity through A(3)-macrocyclization and introducing new components has shown the importance of triple bonds and residues like N-epsilon-allyl lysine in high CD36 binding affinity, aiding in the development of ideal CD36 modulators to curb macrophage-driven inflammation.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Anh Minh Thao Nguyen, Skye Brettell, Noelie Douanne, Claudia Duquette, Audrey Corbeil, Emanuella F. Fajardo, Martin Olivier, Christopher Fernandez-Prada, William D. Lubell
Summary: The study demonstrated that derivatives with a single methyl group in N-methylated lipopeptides exhibit higher activity against various strains of leishmaniasis protozoan and have relatively high potency against resistant strains. Additionally, the systematic study of the effects of methylation and turn geometry on anti-parasitic activity revealed the importance of an extended conformer about the central residues and conformational mobility by tertiary amide isomerization and turn geometry at the extremities of the active peptides.
Article
Chemistry, Organic
Ramakotaiah Mulamreddy, Xin Hou, Sylvain Chemtob, William D. Lubell
Summary: The synthesis of 6-hydroxymethyl indolizidin-2-one amino acids from L-serine involves 10 steps, including intramolecular ring opening and lactam formation. X-ray analyses showed ideal peptide geometry, and the analogue exhibited inhibitory activity on myometrial contractility within a prostaglandin-F-2 alpha receptor modulator.
Article
Biochemistry & Molecular Biology
Ramakotaiah Mulamreddy, William D. Lubell
Summary: This paper reports the synthesis of 5- and 7-hydroxy indolizidin-2-one N-(Boc)amino acids from L-serine, and discusses their potential in peptide mimicry.
Article
Biochemistry & Molecular Biology
John W. R. Schwabe, Andrew G. Jamieson, Lewis J. Archibald, Edward A. Brown, Christopher J. Millard, Peter J. Watson, Naomi S. Robertson, Siyu Wang
Summary: Research suggests that the specific functions of class I HDAC corepressor complexes are partly driven by the recognition of the primary amino acid sequence surrounding a particular lysine position in the histone tail.
ACS CHEMICAL BIOLOGY
(2022)
Editorial Material
Biochemistry & Molecular Biology
William D. Lubell
Article
Chemistry, Medicinal
Xiaozheng Wei, Sitan Diarra, Antoine Douchez, Juliana C. Cunico Dallagnol, Terence E. Hebert, David Chatenet, William D. Lubell
Summary: The study of Urotensin II receptor (UT) modulators can help us understand the roles of the endogenous cyclic peptide ligands urotensin II (UII) and urotensin II-related peptide (URP) in disease etiology. By designing and synthesizing a series of compounds, selective modulators of hUII and URP activities were discovered, which can affect biological processes such as vasoconstriction.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Anh Minh Thao Nguyen, Moran Shalev-Benami, Chloe Rosa-Teijeiro, Ana Victoria Ibarra-Meneses, Ada Yonath, Anat Bashan, Charles L. Jaffe, Martin Olivier, Christopher Fernandez-Prada, William D. Lubell
Summary: A strategy for preparing potent anisomycin derivatives with reduced host toxicity has been revealed by assessing structure-activity relationships for anti-protozoan activity. Different modifications of the alcohol, amine, and aromatic functional groups have been studied, and it was found that introducing substituents at the para-phenol moiety of anisomycin can maintain the anti-protozoan potency without significant loss of activity against the host.
Article
Chemistry, Organic
Zhihong Luo, Lei Xu, Xiaomin Tang, Xuejun Zhao, Tong He, William D. Lubell, Jinqiang Zhang
Summary: In this study, novel all-hydrocarbon cross-linked aza-stapled peptides were designed and synthesized for the first time. These peptides exhibited increased anti-tumor activity, binding affinities, and cell membrane permeability compared to their linear counterparts.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Aisling Minard, Danielle Morgan, Federica Raguseo, Anna Di Porzio, Denise Liano, Andrew G. Jamieson, Marco Di Antonio
CHEMICAL COMMUNICATIONS
(2020)
Article
Biochemistry & Molecular Biology
Fatemeh M. Mir, Marco Crisma, Claudio Toniolo, William D. Lubell