Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization / cleavage step

Dressman, Bruce A.; Spangle, Larry A.; Kaldor, Stephen W.

doi:10.1016/0040-4039(95)02395-x

Cited by 205 publications

(117 citation statements)

References 17 publications

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“…The literature on combinatorial approaches to hydantoins of various types is now comparatively extensive supporting an implicit consensus on the value of hydantoin centroids. [48][49][50][51] The ␤-lactam ring makes an almost ideal centroid (Fig. 12) with its very small molecular weight cost (66), rich adornment possibilities (five sites; an average of six major atoms each), ease of construction, control of sterochemistry by the Staudinger reaction, and its peptide-like character before or after hydrolysis.…”

Section: O M B I N a T O R I A L L I B R A R I E S O F D R U G A N mentioning

confidence: 99%

The search for orally active medications through combinatorial chemistry

Fecik¹,

Frank²,

Gentry³

et al. 1998

Med. Res. Rev.

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Section: O M B I N a T O R I A L L I B R A R I E S O F D R U G A N mentioning

confidence: 99%

The search for orally active medications through combinatorial chemistry

Fecik¹,

Frank²,

Gentry³

et al. 1998

Med. Res. Rev.

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“…Reaction of the solid support with p-nitrophenyl chloroformate gave the active carbonate resin 16 [26] and afterwards the e-amino group of Fmoc-b 3 hLys-OAll·TFA (10) was anchored to the resin in 60 % yield. [27] Just as in the case of tetrapeptide 14, the assembly of the linear, resin bound fully protected b-peptide 18 was carried out following standard peptide synthesis procedures.…”

Section: Resultsmentioning

confidence: 99%

Cyclic β‐Tetra‐ and Pentapeptides: Synthesis through On‐Resin Cyclization and Conformational Studies by X‐Ray, NMR and CD Spectroscopy and Theoretical Calculations

Büttner¹,

Norgren²,

Zhang³

et al. 2005

Chemistry A European J

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The solution-phase synthesis of the simplest cyclic beta-tetrapeptide, cyclo(beta-Ala)4 (4), as well as the solid-phase syntheses through side chain anchoring and on-resin cyclization of the cyclic beta3-tetrapeptide cyclo(-beta3hPhe-beta3hLeu-beta3hLys-beta3hGln-) (14) and the first cyclic beta3-pentapeptide cyclo(-beta3hVal-beta3hPhe-beta3hLeu-beta3hLys-beta3hLys-) (19) are reported. Extensive computational as well as spectroscopic studies, including X-ray and NMR spectroscopy, were undertaken to determine the preferred conformations of these unnatural oligomers in solution and in the solid state. cyclo(beta-Ala)4 (4) with no chiral side chains is shown to exist as a mixture of rapidly interchanging conformers in solution, whereas inclusion of chiral side chains in the cyclo-beta3-tetrapeptide causes stabilization of one dominating conformer. The cyclic beta3-pentapeptide on the other hand shows larger conformational freedom. The X-ray structure of achiral cyclo(beta-Ala)4 (4) displays a Ci-symmetrical 16-membered ring with adjacent C=O and N-H atoms pointing pair wise up and down with respect to the ring plane. CD spectroscopic examinations of all cyclic beta-peptides were undertaken and revealed results valuable as starting point for further structural investigations of these entities.

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“…Glycosylation of 10 with 12 under similar conditions gave 35 % glycosylation and when the procedure was repeated, 57 % yield according to gelphase 19 F NMR spectroscopy. Although the 19 F NMR spectra allowed estimation of the glycosylation yields the spectra were of relatively poor quality. The reason for the strong broadening of the fluorine signals is not known.…”

Section: Synthesis Of Neoglycolipidsmentioning

confidence: 99%

Carbamate Linker Strategy in Solid‐Phase Synthesis of Amino‐Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein‐Carbohydrate Interactions

et al. 2009

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Amino‐functionalized serine‐based galactose and glucose neoglycolipids were prepared by solid‐phase synthesis using a carbamate strategy for anchoring amino functionalities to a (2‐fluoro‐4‐hydroxymethylphenoxy)acetic acid linker resin. Key synthetic steps were monitored with gel‐phase 19F NMR spectroscopy. Cleavage from the solid support was performed with trifluoroacetic acid. The terminal amine of the neoglycolipids was conjugated with didecyl squarate and then immobilized in amino‐functionalized microtiter plates and the glycoconjugates were successfully probed with a galactose‐binding lectin.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization / cleavage step

Cited by 205 publications

References 17 publications

The search for orally active medications through combinatorial chemistry

The search for orally active medications through combinatorial chemistry

Cyclic β‐Tetra‐ and Pentapeptides: Synthesis through On‐Resin Cyclization and Conformational Studies by X‐Ray, NMR and CD Spectroscopy and Theoretical Calculations

Carbamate Linker Strategy in Solid‐Phase Synthesis of Amino‐Functionalized Glycoconjugates for Attachment to Solid Surfaces and Investigation of Protein‐Carbohydrate Interactions

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