Arginine, Histidine and Tryptophan in Peptide Synthesis. The Imidazole Function of Histidine

Rzeszotarska, Barbara; Masiukiewicz, Ełżbieta

doi:10.1080/00304948909356412

Cited by 6 publications

(3 citation statements)

References 120 publications

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“…The NT-isomer was identified unambiguously by NOES between CH-2 (SUC) and H-2, H-4 (His). Again a preference for the z-derivative (about SO',) was observed in full agreement with the ratios found for other P"alkylations and acylations (17). Formation of these two histidine derivatives by reaction with NEM has been postulated previously (8), but in the present study it has been definitely confirmed by NMR analysis.…”

Section: Mal>p-ala-osu + H-ser(tbu)-his-arg(hcl)-ile-ser(tbul-ohsupporting

confidence: 92%

“…1). Alkylation of histidine is known to occur preferentially and in some cases exclusively at the NTposition (17). It is therefore reasonable to assume that in the present case the isomers identified in a correct 1: 1 ratio correspond to the pair of NT-diastereoisomcrs arising from the new chiral center at the C-2 of the succinimidyl moiety.…”

Section: Mal>p-ala-osu + H-ser(tbu)-his-arg(hcl)-ile-ser(tbul-ohmentioning

confidence: 73%

“…Selective grafting of N"-Mal> /?-Ala-HG- [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] to the surface-exposed Cys-107 of iso-1-cytochrome c allowed the presentation of the haptenic gastrin molecule in a unique proteic environment to the immune competent cells. As a result immunization expcriments in rabbits Nim-alkylation of histidine-peptides (14) (1 3) and guinea pigs (14) led to high titers of antigastrin antisera of gastrin receptor-like specificity.…”

Section: Results and Discusslonmentioning

confidence: 99%

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Alkylation of histidine with maleimido‐compounds

Papini

Rudolph

Siglmüller

et al. 1992

International Journal of Peptide and Protein Research

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Introduction of the maleimide function via a spacer into histidine‐containing peptides was found to produce ring closure by nucleophilic addition of the Nim‐imino function of the histidine side‐chain to the activated double bond of the maleimide. As an intramolecular cyciization reaction it proceeds at remarkably higher rates than the bimolecular alkylation of histidine derivatives with N‐ethyl‐maleimide. Correspondingly, in the case of the histidine‐peptides examined only mixtures of the cyclic isomeric compounds were isolated and structurally characterized by 1H‐NMR analysis. As expected, prevention of this reaction in histidine‐containing maleoyl‐peptides can be achieved by Nim‐protection of the imidazole group. However, upon removal of this protection, the reaction takes place again, thus remarkably hampering the usefulness of the maleimide/thiol addition principle in conjugate chemistry for peptides. On the other hand this reaction could represent an interesting new approach for the design of cyclic peptidomimetic analogs.

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Section: Mal>p-ala-osu + H-ser(tbu)-his-arg(hcl)-ile-ser(tbul-ohsupporting

confidence: 92%

Section: Mal>p-ala-osu + H-ser(tbu)-his-arg(hcl)-ile-ser(tbul-ohmentioning

confidence: 73%

Section: Results and Discusslonmentioning

confidence: 99%

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Alkylation of histidine with maleimido‐compounds

Papini

Rudolph

Siglmüller

et al. 1992

International Journal of Peptide and Protein Research

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ChemInform Abstract: Arginine, Histidine, and Tryptophan in Peptide Synthesis. The Imidazole Function in Histidine

Rzeszotarska

Masiukiewicz

1990

ChemInform

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Preparation of Protected β²‐ and β³‐Homocysteine, β²‐ and β³‐Homohistidine, and β²‐Homoserine for Solid‐Phase Syntheses

Lelais

Micuch

Josien‐Lefebvre

et al. 2004

Helvetica Chimica Acta

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The Ser, Cys, and His side chains play decisive roles in the syntheses, structures, and functions of proteins and enzymes. For our structural and biomedical investigations of b-peptides consisting of amino acids with proteinogenic side chains, we needed to have reliable preparative access to the title compounds. The two b 3homoamino acid derivatives were obtained by Arndt ± Eistert methodology from Boc-His(Ts)-OH and Fmoc-Cys(PMB)-OH (Schemes 2 ± 4), with the side-chain functional groups reactivities requiring special precautions. The b 2 -homoamino acids were prepared with the help of the chiral oxazolidinone auxiliary DIOZ by diastereoselective aldol additions of suitable Ti-enolates to formaldehyde (generated in situ from trioxane) and subsequent functional-group manipulations. These include OH 3 O t Bu etherification (for b 2 hSer; Schemes 5 and 6), OH 3 STrt replacement (for b 2 hCys; Scheme 7), and CH 2 OH 3 CH 2 N 3 3 CH 2 NH 2 transformations (for b 2 hHis; Schemes 9 ± 11). Including protection/deprotection/re-protection reactions, it takes up to ten steps to obtain the enantiomerically pure target compounds from commercial precursors. Unsuccessful approaches, pitfalls, and optimization procedures are also discussed. The final products and the intermediate compounds are fully characterized by retention times (t R ), melting points, optical rotations, HPLC on chiral columns, IR, 1 Hand 13 C-NMR spectroscopy, mass spectrometry, elemental analyses, and (in some cases) by X-ray crystalstructure analysis.

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Arginine, Histidine and Tryptophan in Peptide Synthesis. The Imidazole Function of Histidine

Cited by 6 publications

References 120 publications

Alkylation of histidine with maleimido‐compounds

Alkylation of histidine with maleimido‐compounds

ChemInform Abstract: Arginine, Histidine, and Tryptophan in Peptide Synthesis. The Imidazole Function in Histidine

Preparation of Protected β²‐ and β³‐Homocysteine, β²‐ and β³‐Homohistidine, and β²‐Homoserine for Solid‐Phase Syntheses

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Arginine, Histidine and Tryptophan in Peptide Synthesis. The Imidazole Function of Histidine

Cited by 6 publications

References 120 publications

Alkylation of histidine with maleimido‐compounds

Alkylation of histidine with maleimido‐compounds

ChemInform Abstract: Arginine, Histidine, and Tryptophan in Peptide Synthesis. The Imidazole Function in Histidine

Preparation of Protected β2‐ and β3‐Homocysteine, β2‐ and β3‐Homohistidine, and β2‐Homoserine for Solid‐Phase Syntheses

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Product

Resources

About

Preparation of Protected β²‐ and β³‐Homocysteine, β²‐ and β³‐Homohistidine, and β²‐Homoserine for Solid‐Phase Syntheses