Synthesis of carbamates of .alpha.-amino sulfonamides

Gilmore, W. Franklin; Lin, Horng-Jau

doi:10.1021/jo00417a035

Cited by 26 publications

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“…For example, replacement of a peptide amide by a phosphonamide or a silanediol may effectively mimic the tetrahedral transition states common in enzyme-catalyzed reactions and produce enzyme inhibitors. Although the respective amide to sulfonamide exchange may appear promising, the resulting α-sulfonamido peptides have been reported to be unstable …”

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confidence: 99%

“…Although the respective amide to sulfonamide exchange may appear promising, the resulting R-sulfonamido peptides have been reported to be unstable. 3 N-Aminosulfamido peptides 1 in which both the C R H and the carbonyl of an amino acid residue are respectively replaced by a nitrogen atom and a sulfonyl group have proven to be more stable (Figure 1). Moreover, aza-sulfurylphenylalaninyl (Asf) peptide 2 was reported to inhibit the human immunodeficiency virus-1 (HIV-1) proteinase, presumably by imitating the transition state for amide bond hydrolysis.…”

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confidence: 99%

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N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides

2012

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N-Aminosulfamides are peptidomimetics in which the C(α)H and the carbonyl of an amino acid residue are both respectively replaced by a nitrogen atom and a sulfonyl group. Aza-sulfurylglycinyl tripeptide analogs were effectively synthesized from amino acid building blocks by condensations of N-protected amino hydrazides and p-nitrophenylsulfamidate esters. The installation of N-alkyl chains and access to other aza-sulfuryl amino acid residues were effectively achieved by chemoselective alkylation.

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confidence: 99%

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N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides

2012

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“…Sulfonopeptides are sulfur analogues of peptides containing at least one of the two 1-or 2-aminoalkanesulfonic acid or amide residue(s) 1,2 whereby both 1-aminoalkanesulfonic acids and amides are unstable structural moieties. [3][4][5][6][7][8] Actually, sulfonopeptides in the 2-aminoalkanesulfonic acid moiety are close sulfur structural mimetics of β-peptides. 1,2 The sulfonopeptides with the 2-aminoalkanesulfonic acid residue(s) in the N-terminus or internal position are also called sulfonamidopeptides or peptidosulfonamides because they possess the sulfonamide bond.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of sulfonopeptides

2021

Journal of Peptide Science

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Sulfonopeptides as the sulfur analogues of natural peptides have been widely used as enzyme inhibitors due to their tetrahedral sulfonamide moiety, which can mimic the transition‐state analogues of hydrolysis of the ester and amide bonds. Synthetic methods of sulfonopeptides are reviewed. The synthetic methods of sulfonopeptides include the condensation of N‐protected amino acid/peptide acids and 2‐aminoalkanesulfonic acids, coupling of N‐protected 2‐aminoalkanesulfonyl chlorides and amino acid esters/peptide esters, sulfinylation of amino acid esters/peptide esters with N‐protected 2‐aminoalkanesulfinyl chlorides and subsequent oxidation, the alkylation of taurine‐containing peptides, and the displacement of N‐aminoacyl/peptidyl 2‐aminoalkyl halides/methanesulfonates with sulfites. Hybrid sulfonophosphinopeptides are prepared through the Mannich‐type reaction of N‐protected 2‐aminoalkanesulfonamides/peptidylsulfonamides, aldehydes, and aryldichlorophosphines/phosphorus trichloride followed by the aminolysis with amino acid/peptide esters or hydrolysis. The developed synthetic methods provide diverse synthetic routes for biologically important sulfonopeptides as the candidates of medicinal agents.

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“…On the other hand, attempts have been less successful at employing β–aminosulfonamides as tetrahedral mimics in enzyme inhibitors of HIV protease, thermolysin, and thrombin, as well as antigens for raising catalytic antibodies . Notably, the application of α–aminosulfonamides as tetrahedral mimics in enzyme inhibitors has failed due to their rapid decomposition …”

Section: Introductionmentioning

confidence: 99%

crystal structure analyses of azasulfuryltripeptides reveal potential for γ‐turn mimicry^†

Turcotte

Lubell

2015

Biopolymers

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Azasulfurylpeptides feature an amino acid residue in which the CαH and the carbonyl are replaced respectively by a nitrogen atom and a sulfonyl group. Insight into the conformational preferences of azasulfurylpeptides containing an azasulfurylglycine (AsG) residue has been pursued using X-ray analysis in the solid state. Crystals of N-(Boc)-Pro-AsG-Val-OMe (10) and N-(Cbz)-Ala-AsG-D-Phe-Ot-Bu (11) showed tetrahedral geometries about the sulfur atom with the ω torsion angle preferring a staggered conformation. Furthermore, the ϕ and ψ torsion angles of the central azasulfuryl residue were respectively within close proximity to those of ideal inverse and classical γ-turns. In the crystal lattice, azasulfurylpeptide 11 engaged in intermolecular hydrogen bonds between the sulfonyl oxygen and hydrazide hydrogen in an antiparallel orientation.

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Synthesis of carbamates of .alpha.-amino sulfonamides

Cited by 26 publications

References 1 publication

N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides

N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides

Synthesis of sulfonopeptides

crystal structure analyses of azasulfuryltripeptides reveal potential for γ‐turn mimicry^†

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Synthesis of carbamates of .alpha.-amino sulfonamides

Cited by 26 publications

References 1 publication

N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides

N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides

Synthesis of sulfonopeptides

crystal structure analyses of azasulfuryltripeptides reveal potential for γ‐turn mimicry†

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crystal structure analyses of azasulfuryltripeptides reveal potential for γ‐turn mimicry^†