A Stable Pyridinesulfenyl Halide

Matsueda, Rei; Aiba, K.

doi:10.1246/cl.1978.951

Cited by 40 publications

(23 citation statements)

References 2 publications

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“…60 Thereby, conversion of the Cys(Acm) or Cys containing peptide chains into the Cys(Npys) derivatives by reaction with Npys-Cl (Refs. [61][62][63] or (Npys) 2 (Ref. 64), respectively, offered the advantage of high exchange rates with the unprotected cysteine components even under acidic conditions where scrambling of preformed disulfides is prevented.…”

Section: Synthesis Of the Heterotrimersmentioning

confidence: 99%

Synthetic heterotrimeric collagen peptides as mimics of cell adhesion sites of the basement membrane

2004

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Collagen type IV forms a network in the basement membrane into which other constituents of the tissue are incorporated. It also provides cell-adhesion sites that are specifically recognized by cell-surface receptors, i.e., the integrins. Different from the ubiquitous sequential RGD adhesion motif found in most of the matrix proteins, in collagen type IV, the responsible binding sites for alpha1beta1 integrin have been identified as Asp461 of the two alpha1 chains and Arg461 of the alpha2 chain. Because of the heterotrimeric character of this collagen, the spatial geometry of the binding epitope depends not only on the triple-helical fold, but decisively even on the stagger of the chains. To investigate the effects of chain registration on the conformational properties and binding affinities of this adhesion epitope, two synthetic heterotrimeric collagen peptides consisting of the identical three chains were assembled by an artificial cystine knot in two different registers, i.e., in the most plausible alpha2alpha1alpha1' and less probable alpha1alpha2alpha1' chain alignment. A detailed conformational characterization of both trimers allowed to correlate their different binding affinities for alpha1beta1 integrin with the degree of local plasticity of the two different triple helices. Optimal local breathing of the rod-shaped collagens is apparently crucial for selective recognition by proteins interacting with these main components of the extracellular matrix.

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Section: Synthesis Of the Heterotrimersmentioning

confidence: 99%

Synthetic heterotrimeric collagen peptides as mimics of cell adhesion sites of the basement membrane

2004

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“…This sulfenyl chloride has apparently not been used previously for derivatizing alkenes. In fact, it has not been studied extensively as it is reported to be rather unstable in air 29,, 34. However, we found that it was quite possible to work with the reagent for up to several days provided that it was refrigerated and not exposed to moisture for prolonged periods of time.…”

Section: Resultsmentioning

confidence: 88%

“…Although 1 is not commercially available, it is easy to prepare from commercially available 2,2′‐dithiobis(5‐nitropyridine) ( 2 ) by cleavage of the disulfide linkage with chlorine gas as shown in Eqn. (1) 29 …”

Section: Resultsmentioning

confidence: 99%

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Derivatization for electrospray ionization-mass spectrometry. 4. Alkenes and alkynes

Berkel

Quirke

Adams

2000

Rapid Commun. Mass Spectrom.

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A survey of derivatization strategies and prospective derivatization reactions for conversion of simple alkenes and alkynes to 'electrospray-active' species is presented. General synthetic strategies are discussed and illustrative examples of prospective derivatives prepared from model compounds are presented along with their electrospray ionization (ES) mass spectra. The identified derivatives of these neutral, nonpolar analytes are either ionic or are ionizable in solution through Bronsted acid/base chemistry, by Lewis acid/base chemistry, or by chemical or electrochemical electron-transfer chemistry. Once ionized, the derivatives are expected to be amenable to detection by electrospray ionization-mass spectrometry. Derivatives are identified for positive and negative ion analysis of both alkenes and alkynes. Copyright 2000 John Wiley & Sons, Ltd.

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“…BocCys(Npys)OH was synthesized according to published procedures (8,9). BocCys(Npys)OH was synthesized according to published procedures (8,9).…”

Section: Methodsmentioning

confidence: 99%

Novel version of Multiple Antigenic Peptide allowing incorporation on a cysteine functionalized lysine tree

Baleux

Dubois

1992

International Journal of Peptide and Protein Research

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A novel version of Multiple Antigenic Peptide (MAP) is described. This approach consists of the synthesis of a properly functionalized antigen carrier and the incorporation, on request, of one or more activated antigenic peptides. This method was to synthesize a MAP containing eight epitopes of Hsp 70-1 from Plasmodium falciparum. Mice immunised with this MAP gave a specific response while those immunised with the peptide alone did not.

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A Stable Pyridinesulfenyl Halide

Cited by 40 publications

References 2 publications

Synthetic heterotrimeric collagen peptides as mimics of cell adhesion sites of the basement membrane

Synthetic heterotrimeric collagen peptides as mimics of cell adhesion sites of the basement membrane

Derivatization for electrospray ionization-mass spectrometry. 4. Alkenes and alkynes

Novel version of Multiple Antigenic Peptide allowing incorporation on a cysteine functionalized lysine tree

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