Synthesis, Conformational Studies and Binding Properties of Acyclic Receptors for N-Protected Amino Acids and Dipeptides

Botana, Enrique; Ongeri, Sandrine; Arienzo, Rosa; Demarcus, Mariangela; Frey, Jeremy G.; Piarulli, Umberto; Potenza, Donatella; Kilburn, Jeremy D.; Gennari, Cesare

doi:10.1002/1099-0690(200112)2001:24<4625::aid-ejoc4625>3.0.co;2-l

Cited by 10 publications

(1 citation statement)

References 8 publications

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“…[15][16][17] Furthermore, in view of the growing importance of the incorporation of unnatural (and often difficult to couple) building blocks in peptide chains and the often improved results obtained when using the novel PEG based resins, one should be aware that the combination of this novel well-performing resins with OH-sensitive color tests can give rise to false positive results, impeding a correct interpretation of coupling progress and leading to the entirely unnecessary application of double couplings and concurrent waste of precious building blocks. The presence of free hydroxyl groups can further also interfere in other reactions.…”

Section: Resultsmentioning

confidence: 84%

NF-31 color test uncovers ‘hidden’ alcohol functionalities in PEG-based resins for solid phase peptide synthesis

Carrette

Verzele

Madder

2010

Tetrahedron Letters

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During solid phase peptide synthesis on novel aminomethyl-PEG-based resins, undesired coloration of resins was observed during color tests due to the presence of left-over alcohol functionalities in the base resin. These can participate in ongoing reactions and lead to unexplicable outcomes, if not taken into consideration.Leave this area blank for abstract info. Abstract-Recently developed PEG-based resins have been shown to markedly improve the quality of the synthesis in case of so-called 'difficult' peptide sequences. Difficult coupling reactions further require sensitive color tests for amines in the assessment of the completeness of coupling. We here describe how the use of PEG-based resins in combination with one of the more sensitive color tests in SPPS can lead to severe misinterpretation and unnecessary delays during solid phase peptide synthesis due to the presence of 'nondeclared' free hydroxyl functionalities in aminomethyl-PEG-based resins F-31 color test uncovers 'hidden' alcohol functionalities in PEG-based resins for solid phase peptide synthesis

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Section: Resultsmentioning

confidence: 84%

NF-31 color test uncovers ‘hidden’ alcohol functionalities in PEG-based resins for solid phase peptide synthesis

Carrette

Verzele

Madder

2010

Tetrahedron Letters

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Flexible but with a Defined Turn—Influence of the Template on the Binding Properties of Two‐Armed Receptors

Wennemers

Nold

Conza

et al. 2003

Chemistry A European J

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Combinatorial binding studies revealed that the di(trans-4-aminoproline)diketopiperazine is an ideal template for two-armed receptors with highly selective binding properties towards peptides. It is not only superior to structurally very different diamines but also to the diastereomeric di(cis-4-aminoproline)diketopiperazine. These empiric results are rationalized by the analysis of the conformation of the diastereomeric diketopiperazines in the solid state, by X-ray crystal structure analysis, as well as by NMR studies in solution: to observe highly selective binding, the template needs to be not only conformationally rigid but it must have a specific turn geometry. The combination of combinatorial binding studies, X-ray crystal structure analysis, and NMR spectroscopy gave insight into why the trans,trans-diketopiperazine is a superior template compared to other diamines. Additionally, the results provide a guide for the rational design of two-armed receptors with good binding properties towards peptidic guests.

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Synthesis of Functionalized Guanidino Amino Acids

Suhs¹,

König²

2006

Chemistry A European J

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We report the synthesis of guanidino amino acids (GuAA), which are structurally related to Arg and resemble a dipeptide consisting of alpha- and gamma-amino acid with a guanidinium group in the main chain. The compounds are available with different protecting groups in gram amounts and are intended as synthetic building blocks for the construction of synthetic oxoanion or peptide receptors. Tyr, Trp or dansyl-functionalized Lys can be introduced as the alpha-amino acid part, which leads to luminescent GuAAs. The compounds signal carboxylate binding in MeOH, DMSO and buffered water by change of the emission intensity. The property may find use in the construction of chemosensors.

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Synthesis, Conformational Studies and Binding Properties of Acyclic Receptors for N-Protected Amino Acids and Dipeptides

Cited by 10 publications

References 8 publications

NF-31 color test uncovers ‘hidden’ alcohol functionalities in PEG-based resins for solid phase peptide synthesis

NF-31 color test uncovers ‘hidden’ alcohol functionalities in PEG-based resins for solid phase peptide synthesis

Flexible but with a Defined Turn—Influence of the Template on the Binding Properties of Two‐Armed Receptors

Synthesis of Functionalized Guanidino Amino Acids

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