A novel dendrimer-type m-terphenyl substituent for the kinetic stabilization of highly reactive species

Goto, Kei; Yamamoto, Gaku; Tan, Bo; Okazaki, Renji

doi:10.1016/s0040-4039(01)00871-1

Cited by 40 publications

(35 citation statements)

References 15 publications

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“…When this amino group is removed by decapitation to methionine, cross-linking fails. Moreover, the mechanism proposed for this reaction, I 2 oxidation of a thiolate to a sulfenyl halide followed by nucleophilic attack by an amine to form a sulfenamide, makes chemical sense and is known in the synthetic-organic literature (20)(21)(22). It is still unclear whether this cross-link remains a sulfenamide or proceeds to higher oxidation states.…”

Section: Discussionmentioning

confidence: 99%

CLC Cl ⁻ /H ⁺ transporters constrained by covalent cross-linking

Nguitragool

Miller

2007

Proc. Natl. Acad. Sci. U.S.A.

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This contribution is part of the special series of Inaugural Articles by members of the National Academy of Sciences elected on May 1, 2007.CLC Cl ؊ /H ؉ exchangers are homodimers with Cl ؊ -binding and H ؉ -coupling residues contained within each subunit. It is not known whether the transport mechanism requires conformational rearrangement between subunits or whether each subunit operates as a separate exchanger. We designed various cysteine substitution mutants on a cysteine-less background of CLC-ec1, a bacterial CLC exchanger of known structure, with the aim of covalently linking the subunits. The constructs were cross-linked in air or with exogenous oxidant, and the cross-linked proteins were reconstituted to assess their function. In addition to conventional disulfides, a cysteine-lysine cross-bridge was formed with I 2 as an oxidant. The constructs, all of which contained one, two, or four cross-bridges, were functionally active and kinetically competent with respect to Cl ؊ turnover rate, Cl ؊ /H ؉ exchange stoichiometry, and H ؉ pumping driven by a Cl ؊ gradient. These results imply that large quaternary rearrangements, such as those known to occur for ''common gating'' in CLC channels, are not necessary for the ion transport cycle and that it is therefore likely that the transport mechanism is carried out by the subunits working individually, as with ''fast gating'' of the CLC channels.disulfide ͉ oxidation ͉ sulfenamide ͉ antiporter ͉ exchanger

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Section: Discussionmentioning

confidence: 99%

CLC Cl ⁻ /H ⁺ transporters constrained by covalent cross-linking

Nguitragool

Miller

2007

Proc. Natl. Acad. Sci. U.S.A.

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“…To embody this concept, we have designed four types of bowl‐shaped molecules having substituents Ar 1 ‐, Ar 2 ‐, Bmt‐, and Bpq‐ and succeeded in the synthesis of stable compounds bearing some highly reactive functionalities, which are very susceptible to self‐dimerization, such as sulfenic acids (Ar 1 SOH 52 , Ar 2 SOH , BmtSOH ), selenenic acid (Ar 2 SeOH 53 , BmtSeOH ), sulfenyl iodide (BmtSI 54 , BpqSI ), and nitrosothiol (BpqSNO 55 , BmtSNO ) (Chart ). As anticipated, all of these compounds are quite stable toward dimerization, yet capable of reacting with relatively small molecules that can enter their cavities.…”

Section: Synthesis Of Heteroatom‐containing Reactive Species By Takinmentioning

confidence: 99%

Kinetic Stabilization of Highly Reactive Species Bearing Heteroatoms

Okazaki¹

2014

Heteroatom Chemistry

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“…For preparation of TRIP, the use of t-butyllithium instead of n-butyllithium for lithiation of bromide 5 [8] gave better results, although the yield was moderate. Usually, the compounds composed of oligophenylene units show poor solubility, which is one of the largest problems of such kind of aromatic compounds.…”

Section: Syntheses Of Triarylphosphines Trmp and Tripmentioning

confidence: 99%