Sugar furanoid trans-vicinal diacid as a γ-turn inducer: synthesis and conformational study

Vangala, Madhuri; Dhokale, Snehal; Gawade, Rupesh L.; Pattuparambil, Rajamohanan R.; Puranik, Vedavati G.; Dhavale, Dilip D.

doi:10.1039/c3ob41462k

Cited by 15 publications

(10 citation statements)

References 54 publications

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“…D-Glucose was converted to C3-tetrasubstituted furanoid sugar azido ester 3 as per our reported protocol [12]. Hydrolysis of ester functionality in 3 using LiOH in THF:H2O:MeOH at room temperture afforded azido acid 4a (90%) while; The azido ester dipeptide 5 and tetrapeptide 7 were individually converted to amino acid di-and tetra-peptides 8 and 9 respectively, using hydrolysis followed by hydrogenation reaction protocol (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

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Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Burade¹,

Pawar²,

Saha³

et al. 2019

Preprint

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The C3-tetrasubstituted furanoid sugar amino acid derived linear amino acid dipeptide 8 and tetrapeptide 9 on intra-molecular cyclization afforded oxazolone pseudo-peptides 1 and 2a, respectively, with formation of oxazole ring at the C-terminus. Conformational study of 2a showed seven membered intramolecular C=O×××HN (II) hydrogen bonding leading to the γ-turn conformation which is absent in the precursor tetrapeptide 9 thus indicating the role of oxazolone ring in γ-turn formation in 2a. This fact was supported by the molecular modeling studies. The oxazolone ring containing pseudo-tetrapeptide 2a was found to be better ion transporter than pseudodi-peptide1.The ion selectivity of 2a indicated Cl-anion-selective transport via the antiport mechanism.

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Section: Resultsmentioning

confidence: 99%

“…sequence (H-Phe-Trp-Lys-Thy-OH) to get glycopeptide which acts as a α-turn inducer [12]. Recently, our group has synthesized acyclic-and cyclic-fluorinated peptides from C-3 fluorinated D-glucofuranoid amino acid and demonstrated their selective anion transport activity [13][14].…”

Section: Introductionmentioning

confidence: 99%

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Burade¹,

Pawar²,

Saha³

et al. 2019

Preprint

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“…Stick and co-workers have reported the synthesis of tetrasubstituted sugar furanoid amino acid (TSFAA)-derived homologated linear pentapeptide which showed a well defined intramolecular hydrogen-bonding-stabilized helical array [9–11]. Our group has reported a trans -vicinal ᴅ-glucofuranoroic-3,4-diacid with a TAA framework and incorporated it into the N -terminal tetrapeptide sequence (H-Phe-Trp-Lys-Thy-OH) to get a glycopeptide which acts as an α-turn inducer [12]. Over the last several years, synthetic peptides are known to play a significant role in the design of artificial ion transport systems [13–16].…”

Section: Introductionmentioning

confidence: 99%

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

Burade

Pawar

Saha

et al. 2019

Beilstein J. Org. Chem.

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The intramolecular cyclization of a C-3-tetrasubstituted furanoid sugar amino acid-derived linear tetrapeptide afforded an oxazolone pseudo-peptide with the formation of an oxazole ring at the C-terminus. A conformational study of the oxazolone pseudo-peptide showed intramolecular C=O···HN(II) hydrogen bonding in a seven-membered ring leading to a γ-turn conformation. This fact was supported by a solution-state NMR and molecular modeling studies. The oxazolone pseudotetrapeptide was found to be a better Cl−-selective transporter for which an anion–anion antiport mechanism was established.

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“…Despite the use of various Lewis acid catalysts, gold(III)-catalyzed azidation reactions remain rather underexplored till date. In our efforts towards the syntheses of glycoderivatives [ 54 – 56 ], we found that AuBr 3 activates per- O -acetylated and per- O -benzoylated sugars towards anomeric azidation in good to excellent yields.…”

Section: Introductionmentioning

confidence: 99%

AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

Rajput

Hotha

Vangala

2018

Beilstein J. Org. Chem.

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Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr3 in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1–3 h at room temperature, the per-O-benzoylated disaccharides needed 2–3 h of heating at 55 °C.

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Sugar furanoid trans-vicinal diacid as a γ-turn inducer: synthesis and conformational study

Cited by 15 publications

References 54 publications

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

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Sugar furanoid trans-vicinal diacid as a γ-turn inducer: synthesis and conformational study

Cited by 15 publications

References 54 publications

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Sugar Derived Oxazolone Pseudotetrapeptide as γ-Turn Inducer and Anion-Selective Transporter

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

AuBr3-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

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AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars