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Chapter 6 peptide 1 and the PNA trimer 2 were purified by RP-HPLC and characterized by ESI-mass spectrometry. A Boc submonomer strategy was used for the modified PNA 3, in order to better preserve the optical purity at the 2 position 30 . The submonomers were prepared from the corresponding commercial Boc-L-amino acids suitably protected on the side chains. The Boc-L-Lysine-(2- Cl-Z)-OH, to be used as synthon for inserting the lysine side chains in positions 5, was transformed in the corresponding Weinreb amide and then reduced to the aldehyde. Boc-L- Lys-(2-Cl-Z)-OH, Boc-L-Arg-(Tos)-OH and Boc-L-Val were transformed in the corrsponding methyl esters and Boc deprotected by using HCl/MeOH. The PNA backbones were then synthesized by reductive amination on L-amino acid methyl esters with the Boc-L- Lys-(2-Cl-Z) aldehyde. The methyl esters were hydrolyzed and the secondary amines were protected by the introduction of a Fmoc group. All the compounds were characterized by 1 H and 13 C NMR and ESI mass spectrometry. According to the previously reported procedures30, the chiral submonomers units were inserted by manual coupling with the HATU/DIEA protocol on a MBHA-PS resin and, after Fmoc deprotection, the nucleobase residues were introduced by a double coupling with DIC/DhBTOH. After the cleavage from the resin, the PNA trimer 3 was purified by RP- HPLC and characterized by ESI-mass spectrometry (Figure 6-4). 118
PNAs embedding NLS peptide Figure 6-4: HPLC profiles and mass spectra of the synthesized PNAs 119
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Università degli studi di Parma Do
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2.4.4 Fluorescence measurements ...
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Chapter 6 The double nature of Pept
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Preface In Chapter 2 a particular t
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Chapter 1 PNAs: From birth to adult
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PNAs: from birth to adulthood one,
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PNAs: from birth to adulthood betwe
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PNAs: from birth to adulthood explo
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PNAs: from birth to adulthood well,
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PNAs: from birth to adulthood + Res
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PNAs: from birth to adulthood repet
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PNAs: from birth to adulthood 1.6 M
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PNAs: from birth to adulthood amino
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PNAs: from birth to adulthood Cycli
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PNAs: from birth to adulthood DNA a
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PNAs: from birth to adulthood 1.7 C
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PNAs: from birth to adulthood Submo
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PNAs: from birth to adulthood beaco
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PNAs: from birth to adulthood DNA s
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PNAs: from birth to adulthood this
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PNAs: from birth to adulthood 42 C.
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Chapter 2 Label-free detection of S
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PNA Molecular Beacons Figure 2-1: S
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PNA Molecular Beacons DNA is added,
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PNA Molecular Beacons the affinitie
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PNA Molecular Beacons In particular
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PNA Molecular Beacons The sample th
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PNA Molecular Beacons pipetting to
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PNA Molecular Beacons The mastermix
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Chapter 3 A new class of Chiral PNA
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Arginine-PNAs monomers in the middl
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Arginine-PNAs The synthesis of the
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Arginine-PNAs yield in this reactio
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Arginine-PNAs (increased electrosta
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Arginine-PNAs chain + Boc methyl gr
Page 73 and 74: Arginine-PNAs foam. Yield: 30%. 1 H
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Page 77 and 78: Arginine-PNAs PNAs was carried out
Page 79 and 80: Chapter 4 Chiral PNA application on
Page 81 and 82: Arg-PNA Microarrays a surface. Alth
Page 83 and 84: Arg-PNA Microarrays 4.2 Results and
Page 85 and 86: Arg-PNA Microarrays Figure 4-2: HPL
Page 87 and 88: Arg-PNA Microarrays PNA-microarray
Page 89 and 90: Arg-PNA Microarrays Table 4-2. Geno
Page 91 and 92: Arg-PNA Microarrays complex mixture
Page 93 and 94: Arg-PNA Microarrays hybridisation e
Page 95: Arg-PNA Microarrays 30 T. Tedeschi,
Page 98 and 99: Chapter 5 5.1 Introduction The incr
Page 100 and 101: Chapter 5 be printed, in order to m
Page 102 and 103: Chapter 5 Table 5-1. PNA sequences
Page 104 and 105: Chapter 5 printing the PNA on a gla
Page 106 and 107: Chapter 5 22.4°C 24.0°C 25.5°C 2
Page 108 and 109: Chapter 5 PNA 3 PNA 5 PNA 6 Slide 1
Page 110 and 111: Chapter 5 times. The substrates wer
Page 112 and 113: Chapter 5 chemicals were used as re
Page 114 and 115: Chapter 5 5.4.6 Microcontact Printi
Page 116 and 117: Chapter 5 5.5 References 1 A. L. Be
Page 118 and 119: Chapter 6 6.1 Introduction The use
Page 120 and 121: Chapter 6 Among all the peptides us
Page 122 and 123: Chapter 6 Figure 6-2: A standard PN
Page 126 and 127: Chapter 6 6.2.2 Uptake experiments
Page 128 and 129: Chapter 6 (HBTU), N-[(dimethylamino
Page 130 and 131: Chapter 6 1.41 (s, 9H, Boc methyl g
Page 132 and 133: Chapter 6 Arg + CHα Lys), 4.0-4.6
Page 134 and 135: Chapter 6 12 B. P. Gangamani, V. A.
Page 136 and 137: Contributions Publications includin
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