@mastersthesis{MTMT:31598345,
	title = {C-3 epimer cukoraminosavak és új típusú foldamereik szintézise, szerkezetvizsgálata},
	url = {https://m2.mtmt.hu/api/publication/31598345},
	author = {Nagy, Adrienn},
	doi = {10.15476/ELTE.2019.231},
	publisher = {Eötvös Loránd University},
	unique-id = {31598345},
	year = {2020}
}

@article{MTMT:30937506,
	title = {Assignment of Vibrational Circular Dichroism Cross-Referenced Electronic Circular Dichroism Spectra of Flexible Foldamer Building Blocks: Towards Assigning Pure Chiroptical Properties of Foldamers},
	url = {https://m2.mtmt.hu/api/publication/30937506},
	author = {Farkas, Viktor and Nagy, Adrienn and Karancsiné Menyhárd, Dóra and Perczel, András},
	doi = {10.1002/chem.201903023},
	journal-iso = {CHEM-EUR J},
	journal = {CHEMISTRY-A EUROPEAN JOURNAL},
	volume = {25},
	unique-id = {30937506},
	issn = {0947-6539},
	year = {2019},
	eissn = {1521-3765},
	pages = {14890-14900},
	orcid-numbers = {Farkas, Viktor/0000-0002-8815-2783; Karancsiné Menyhárd, Dóra/0000-0002-0095-5531; Perczel, András/0000-0003-1252-6416}
}

@article{MTMT:30859729,
	title = {Unwanted hydrolysis or alpha/beta-peptide bond formation: how long should the rate-limiting coupling step take?},
	url = {https://m2.mtmt.hu/api/publication/30859729},
	author = {Goldschmidt Gőz, Viktória and Nagy, Adrienn and Farkas, Viktor and Keszei, Ernő and Perczel, András},
	doi = {10.1039/c9ra06124j},
	journal-iso = {RSC ADV},
	journal = {RSC ADVANCES},
	volume = {9},
	unique-id = {30859729},
	issn = {2046-2069},
	abstract = {Nowadays, in Solid Phase Peptide Synthesis (SPPS), being either manual, automated, continuous flow or microwave-assisted, the reaction with various coupling reagents takes place via in situ active ester formation. In this study, the formation and stability of these key active esters were investigated with time-resolved H-1 NMR by using the common PyBOP/DIEA and HOBt/DIC coupling reagents for both alpha- and beta-amino acids. Parallel to the amide bond formation, the hydrolysis of the alpha/beta-active esters, a side reaction that is a considerable efficacy limiting factor, was studied. Based on the chemical nature/constitution of the active esters, three amino acid categories were determined: (i) the rapidly hydrolyzing ones (t < 6 h) with smaller (Ala) or even longer side chains (Arg) holding a large protecting group; (ii) branched amino acids (Ile, Thr) with slowly hydrolyzing (6 < t < 24 h) propensities, and (iii) non-hydrolyzing ones, such as the hard-to-couple beta-amino acids or beta-sugar amino acid derivatives, stable for longer times (t > 24 h) in solution. The current insight into the kinetics of this key hydrolysis side reaction serves as a guide to optimize the coupling conditions of alpha- and beta-amino acids, thereby saving time and minimizing the amounts of reagents and amino acids to be used - all key factors of more environmentally friendly chemistry.},
	keywords = {REAGENTS; SOLID-PHASE SYNTHESIS; DRUG DISCOVERY},
	year = {2019},
	eissn = {2046-2069},
	pages = {30720-30728},
	orcid-numbers = {Goldschmidt Gőz, Viktória/0000-0002-9860-2215; Farkas, Viktor/0000-0002-8815-2783; Keszei, Ernő/0000-0002-1458-5201; Perczel, András/0000-0003-1252-6416}
}

@article{MTMT:30435771,
	title = {α/β-Chimera peptide synthesis with cyclic β-sugar amino acids: the efficient coupling protocol},
	url = {https://m2.mtmt.hu/api/publication/30435771},
	author = {Nagy, Adrienn and Goldschmidt Gőz, Viktória and Pintér, István and Farkas, Viktor and Perczel, András},
	doi = {10.1007/s00726-019-02702-9},
	journal-iso = {AMINO ACIDS},
	journal = {AMINO ACIDS},
	volume = {51},
	unique-id = {30435771},
	issn = {0939-4451},
	abstract = {The synthesis of α/β-chimeras comprises peptide bond formation from α- to β-, from β- to β-, and from β- to α-amino acid residues. The fine-tuned solid phase synthesis of –GXXG– chimera peptides containing the simplest achiral α-amino acid glycine and two cyclic SAAs of different ring size [X denoting cyclic β-Sugar Amino Acids (β-SAA)] is reported, variants containing Fmoc–RibAFU(ip)–OH a furanoid-, and Fmoc–GlcAPU(Me)–OH a pyranoid-type structural “Lego-element”. Systematic search for the best coupling strategy with both H–β-SAA–OHs is described, including the comparison of the different coupling reagents and conditions. Selecting the optimal reagent (from commonly used PyBOP, HATU and HOBt) was assisted by time-resolved 1H-NMR: formation and stability of the Fmoc protected active esters were compared. We found that PyBOP is the best choice for successfully coupling both H–β-SAA–OH prototypes. The present comparative results open a reasonable route for building efficiently various –β-SAA– containing homo- and heterooligomers.},
	year = {2019},
	eissn = {1438-2199},
	pages = {669-678},
	orcid-numbers = {Farkas, Viktor/0000-0002-8815-2783; Perczel, András/0000-0003-1252-6416}
}

@article{MTMT:3134571,
	title = {C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies},
	url = {https://m2.mtmt.hu/api/publication/3134571},
	author = {Nagy, Adrienn and Csordás, Barbara and Zsoldos-Mády, Virág and Pintér, István and Farkas, Viktor and Perczel, András},
	doi = {10.1007/s00726-016-2346-5},
	journal-iso = {AMINO ACIDS},
	journal = {AMINO ACIDS},
	volume = {49},
	unique-id = {3134571},
	issn = {0939-4451},
	abstract = {To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–t X–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–c X–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –t X– or –c X– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–t X–Aaa– or –Aaa–t X–t X–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–c X–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.},
	year = {2017},
	eissn = {1438-2199},
	pages = {223-240},
	orcid-numbers = {Farkas, Viktor/0000-0002-8815-2783; Perczel, András/0000-0003-1252-6416}
}

@article{MTMT:3098290,
	title = {Origin of problems related to Staudinger reduction in carbopeptoid syntheses},
	url = {https://m2.mtmt.hu/api/publication/3098290},
	author = {Csordás, Barbara and Nagy, Adrienn and Harmat, Veronika and Zsoldos-Mády, Virág and Leveles, Ibolya and Pintér, István and Farkas, Viktor and Perczel, András},
	doi = {10.1007/s00726-016-2289-x},
	journal-iso = {AMINO ACIDS},
	journal = {AMINO ACIDS},
	volume = {48},
	unique-id = {3098290},
	issn = {0939-4451},
	abstract = {We report the solid phase synthesis of –GG-X-GG– type α/β-carbopeptoids incorporating RibAFU(ip) (1a, tX) or XylAFU(ip) (2a, cX) sugar amino acids. Though coupling efficacy is moderate, both the lengthier synthetic route using Fmoc derivative (e.g., Fmoc-RibAFU(ip)-OH) and the azido derivative (e.g., N3-RibAFU(ip)-OH) via Staudinger reaction with nBu3P can be successfully applied. Both X-ray diffraction, 1H- and 31P-NMR, and theoretical (QM) data support and explain why the application of Ph3P as Staudinger reagent is “ineffective” in the case of a cis stereoisomer, if cX is attached to the preceding residue with a peptide (–CONH–) bond. The failure of the polypeptide chain elongation with N3-cX originates from the “coincidence” of a steric crowdedness and an electronic effect disabling the mandatory nucleophilic attack during the hydrolysis of a quasi penta-coordinated triphenylphosphinimine. Nevertheless, the synthesis of the above α/β-chimera peptides as completed now by a new pathway via 1,2-O-isopropylidene-3-azido-3-deoxy-ribo- and -xylo-furanuronic acid (H-RibAFU(ip)-OH 1a and H-XylAFU(ip)-OH 2a) coupled with N-protected α-amino acids on solid phase could serve as useful examples and starting points of further synthetic efforts. © 2016 Springer-Verlag Wien},
	keywords = {STAUDINGER REACTION; Iminophosphorane; Sugar amino acids; Carbopeptoids},
	year = {2016},
	eissn = {1438-2199},
	pages = {2619-2633},
	orcid-numbers = {Harmat, Veronika/0000-0002-1866-9904; Farkas, Viktor/0000-0002-8815-2783; Perczel, András/0000-0003-1252-6416}
}