Cleavage and deprotection of peptides on MBHA‐resin with hydrogen bromide

Wang, S.S.; Wang, B.S.H.; Hughes, John L.; Leopold, Eric J.; Wu, Chun‐Yi; Tam, James P.

doi:10.1111/j.1399-3011.1992.tb00310.x

Cited by 8 publications

(5 citation statements)

References 25 publications

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“…The peptides were assembled using the standard t-Boc SPPS (solid-phase peptide synthesis) strategy on a MBHA ( p -methylbezhydrilamide) resin [26]. Purity was checked by HPLC.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Nucleic-acid-binding properties of the C2-L1Tc nucleic acid chaperone encoded by L1Tc retrotransposon

Heras

Thomas

Macías

et al. 2009

Biochemical Journal

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It has been reported previously that the C2-L1Tc protein located in the Trypanosoma cruzi LINE (long interspersed nuclear element) L1Tc 3′ terminal end has NAC (nucleic acid chaperone) activity, an essential activity for retrotransposition of LINE-1. The C2-L1Tc protein contains two cysteine motifs of a C2H2 type, similar to those present in TFIIIA (transcription factor IIIA). The cysteine motifs are flanked by positively charged amino acid regions. The results of the present study show that the C2-L1Tc recombinant protein has at least a 16-fold higher affinity for single-stranded than for double-stranded nucleic acids, and that it exhibits a clear preference for RNA binding over DNA. The C2-L1Tc binding profile (to RNA and DNA) corresponds to a non-co-operative-binding model. The zinc fingers present in C2-L1Tc have a different binding affinity to nucleic acid molecules and also different NAC activity. The RRR and RRRKEK [NLS (nuclear localization sequence)] sequences, as well as the C2H2 zinc finger located immediately downstream of these basic stretches are the main motifs responsible for the strong affinity of C2-L1Tc to RNA. These domains also contribute to bind single- and double-stranded DNA and have a duplex-stabilizing effect. However, the peptide containing the zinc finger situated towards the C-terminal end of C2-L1Tc protein has a slight destabilization effect on a mismatched DNA duplex and shows a strong preference for single-stranded nucleic acids, such as C2-L1Tc. These results provide further insight into the essential properties of the C2-L1Tc protein as a NAC.

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“…The peptides were assembled using the standard t-Boc SPPS (solid-phase peptide synthesis) strategy on a MBHA ( p -methylbezhydrilamide) resin [26]. Purity was checked by HPLC.…”

Section: Methodsmentioning

confidence: 99%

“…Peptides were synthesized by the simultaneous multiple solid-phase synthetic method [ 25 ]. The peptides were assembled using the standard t-Boc SPPS (solid-phase peptide synthesis) strategy on a MBHA ( p -methylbezhydrilamide) resin [ 26 ]. Purity was checked by HPLC.…”

Section: Methodsmentioning

confidence: 99%

Nucleic-acid-binding properties of the C2-L1Tc nucleic acid chaperone encoded by L1Tc retrotransposon

Heras

Thomas

Macías

et al. 2009

Biochemical Journal

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“…On completion of the synthesis, dusquetide was detached from the resin by reaction with the in situ generated HBr reagent (HBr 2.8 wt%, entry #4, Table 1) under the optimised conditions previously described. However, according to other studies on peptides cleaved directly from MBHA resin using HBr or TMSBr [10,30], the reaction time was increased to 90 min to ensure the complete peptide release from the resin. Regarding the RR4 heptapeptide, the cleavage reagent was prepared with triisoproylsilane (TIS) instead of TES to prevent the indole ring reduction in the Trp residue (Scheme 2).…”

Section: Acidicmentioning

confidence: 99%

“…resin using HBr or TMSBr [10,30], the reaction time was increased to 90 min to ensure the complete peptide release from the resin. Regarding the RR4 heptapeptide, the cleavage reagent was prepared with triisoproylsilane (TIS) instead of TES to prevent the indole ring reduction in the Trp residue (Scheme 2).…”

Section: Acidicmentioning

confidence: 99%

Linker-Free Synthesis of Antimicrobial Peptides Using a Novel Cleavage Reagent: Characterisation of the Molecular and Ionic Composition by nanoESI-HR MS

et al. 2023

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The efficient preparation of novel bioactive peptide drugs requires the availability of reliable and accessible chemical methodologies together with suitable analytical techniques for the full characterisation of the synthesised compounds. Herein, we describe a novel acidolytic method with application to the synthesis of cyclic and linear peptides involving benzyl-type protection. The process consists of the in situ generation of anhydrous hydrogen bromide and a trialkylsilyl bromide that acts as protic and Lewis acid reagents. This method proved to be useful to effectively remove benzyl-type protecting groups and cleave Fmoc/tBu assembled peptides directly attached to 4-methylbenzhydrylamine (MBHA) resins with no need for using mild trifluoroacetic acid labile linkers. The novel methodology was successful in synthesising three antimicrobial peptides, including the cyclic compound polymyxin B3, dusquetide, and RR4 heptapeptide. Furthermore, electrospray mass spectrometry (ESI-MS) is successfully used for the full characterisation of both the molecular and ionic composition of the synthetic peptides.

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“…The group is usually cleaved by hydrofluoric acid (HF) but can also be cleaved using milder conditions, e. g. tetrafluoroboric acid in triflouroacetic acid or hydroboric acid in acetic acid eliminating the need of special HF apparatuses. [166][167][168] Mbzl protected cysteine was introduced as beforehand in Gly6 position and alternatively an N-terminal polyethylene glycol (PEG) linker was utilised to further attach one Mbzl protected cysteine at the N-terminus directing away from the active binding site. In contrast to N-terminal elongated alkyne modified µ-SIIIA 8 the N-terminal pGlu was preserved, to protect peptides from proteolytic digestion.…”

Section: Synthesis Of Thiol Modified µ-Conotoxin Siiiamentioning

confidence: 99%

Synthesis of fluorescent toxin and nucleotide derivatives to specifically address membrane proteins

Radzey¹

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Cleavage and deprotection of peptides on MBHA‐resin with hydrogen bromide

Cited by 8 publications

References 25 publications

Nucleic-acid-binding properties of the C2-L1Tc nucleic acid chaperone encoded by L1Tc retrotransposon

Nucleic-acid-binding properties of the C2-L1Tc nucleic acid chaperone encoded by L1Tc retrotransposon

Linker-Free Synthesis of Antimicrobial Peptides Using a Novel Cleavage Reagent: Characterisation of the Molecular and Ionic Composition by nanoESI-HR MS

Synthesis of fluorescent toxin and nucleotide derivatives to specifically address membrane proteins

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