Fluoroolefin dipeptide isosteres — I.

Allmendinger, Thomas; Furet, Pascal; Hungerbühler, Ernst

doi:10.1016/s0040-4039(00)88548-2

Cited by 124 publications

(25 citation statements)

References 15 publications

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“…The fluoroolefin dipeptide isostere was proposed as early as 1984 (51) as a superior isoelectronic and isosteric replacement for the amide bond. Theoretical studies strongly have supported the original hypothesis behind introduction of the fluoroolefin amide surrogate (52)(53)(54). The syntheses of fluoroolefin dipeptide surrogates, Ala-[CFϭC]-Pro containing N,O-diacylhydroxamic acid type protease inhibitors 1 and 2, were reported recently by our laboratory (55).…”

mentioning

confidence: 72%

Inhibition of dipeptidyl peptidase IV by fluoroolefin-containingN-peptidyl-O-hydroxylamine peptidomimetics

Lin

Toscano

Welch

1998

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

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Dipeptidyl peptidase IV (EC 3.4.14.5; DPP IV), also known as the leukocyte differentiation antigen CD26 when found as an extracellular membrane-bound proline specific serine protease, cleaves a dipeptide from the N terminus of a polypeptide chain containing a proline residue in the penultimate position. Here we report that known (Z)-Ala-[CF‫؍‬C]-Pro dipeptide isosteres 1 and 2, which contain O-acylhydroxylamines, were isolated as diastereomeric pairs u-1, l-1, and l-2. The effect of each diastereomeric pair as an inhibitor of human placental dipeptidyl peptidase DPP IV has been examined. The inhibition of DPP IV by these compounds is rapid and efficient. The diastereomeric pair u-1 exhibits very potent inhibitory activity with a K i of 188 nM. Fluoroolefin containing N-peptidyl-O-hydroxylamine peptidomimetics, by virtue of their inhibitory potency and stability, are superior to N-peptidyl-O-hydroxylamine inhibitors derived from an Ala-Pro dipeptide.

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mentioning

confidence: 72%

Inhibition of dipeptidyl peptidase IV by fluoroolefin-containingN-peptidyl-O-hydroxylamine peptidomimetics

Lin

Toscano

Welch

1998

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

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“…Such amines have received attention from industrial research groups [24]. The corresponding carbamates were tested as peptide isosteres [25][26][27].…”

Section: Transimination Reactions With A-fluoroacrylonitrilesmentioning

confidence: 99%

α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones

Steenis

Nieuwendijk

Gen

2004

Journal of Fluorine Chemistry

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“…As shown in Figure 1, HWE reactions with 1 have been successfully applied to the syntheses of fluoro-olefin analogues of biologically active compounds such as fluororetinal, [7] 5-fluoroarachidonic acid, [8] a hypothemycin analogue, [9] dipeptide isosteres, [10,11] a selective dipeptidyl peptidase II (DPP II) inhibitor, [12] and a fluoro-olefin analogue of a peptide-nucleic acid (PNA). [13] In an early work on the Z-selective synthesis of fluoroalkenoic acid derivatives, Grison and Sauvêtre reported the reactions between aromatic aldehydes and the dianion derived from α-fluoro-α-phosphorylacetic acid and nBuLi.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Methods for Fluorinated Olefins

2011

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Fluoro‐olefin compounds, because of their favorable physicochemical properties, have been used as key materials in the fields of medicinal chemistry, chemical biology, and materials sciences. A number of the synthetic methodologies for applications of fluoro‐olefin compounds were developed simultaneously. This review article provides an overview not only of recent progress in syntheses of fluoro‐olefin compounds but also of some classical but still valuable synthetic reactions.

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Fluoroolefin dipeptide isosteres — I.

Cited by 124 publications

References 15 publications

Inhibition of dipeptidyl peptidase IV by fluoroolefin-containingN-peptidyl-O-hydroxylamine peptidomimetics

Inhibition of dipeptidyl peptidase IV by fluoroolefin-containingN-peptidyl-O-hydroxylamine peptidomimetics

α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones

Synthetic Methods for Fluorinated Olefins

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