Synthesis of N-urethane protected amino alkyl (S-methyl)-isothiouronium compounds and carbodiimide tethered peptidomimetics: an application for guanidino and substituted guanidino peptidomimetics synthesis

Hosamani, Basavaprabhu; Narendra, N.; Prabhu, Girish; Sureshbabu, Vommina V.

doi:10.1039/c4ra07252a

Cited by 6 publications

(3 citation statements)

References 51 publications

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“…22 For example, aromatic oligomeric N,N'-dimethyl-N,N'-diphenyl guanidines have been reported to fold into well-defined layered structures akin to that of corresponding aromatic oligoureas. Aliphatic oligomers with guanidinium backbones have also been developed as oligonucleotide [23][24][25][26] and peptide 27,28 mimics.…”

Section: Introductionmentioning

confidence: 99%

“…For example, aromatic oligomeric N , N ′-dimethyl- N , N ′-diphenylguanidines have been reported to fold into well-defined layered structures akin to those of the corresponding aromatic oligoureas. Aliphatic oligomers with guanidinium backbones have also been developed as oligonucleotide − and peptide , mimics. Several solid-phase synthesis approaches to access aliphatic oligomeric guanidines have been reported, and the most effective methods are based on the use of arylsulfonyl (e.g., Pbf = (2,2,4,6,7-pentamethyldihydrobenzofuran-5-yl)sulfonyl) and alkoxycarbonyl (e.g., Fmoc = [(9-fluorenylmethyl)oxy]carbonyl, Cbz = carbobenzoxyl, and Troc = (trichloroethoxy)carbonyl) activated thiourea monomers. ,− In these studies, the guanidylation reaction generally involves the transformation of the thiourea moiety into a carbodiimide by treatment with EDC, Mukaiyama reagent, or HgCl 2 in the presence of TEA and subsequent reaction with the terminal amine of the growing chain .…”

Section: Introductionmentioning

confidence: 99%

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Postelongation Strategy for the Introduction of Guanidinium Units in the Main Chain of Helical Oligourea Foldamers

et al. 2018

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The synthesis of hybrid urea-based foldamers containing isosteric guanidinium linkages at selected positions in the sequence is described. We used a postelongation approach whereby the guanidinium moiety is introduced by direct transformation of a parent oligo(urea/thiourea) foldamer precursor. The method involves activation of the thiourea by treatment with methyl iodide and subsequent reaction with amines. To avoid undesired cyclization with the preceding urea moiety, resulting in heterocyclic guanidinium formation in the main chain, the urea unit preceding the thiourea unit in the sequence was replaced by an isoatomic and isostructural γ-amino acid. The approach was extended to solid-phase techniques to accelerate the synthesis of longer and more functionalized sequences. Under optimized conditions, an octamer hybrid oligomer incorporating a central guanidinium linkage was obtained in good overall yield and purity. This work also reports data related to the structural consequences of urea by guanidinium replacements in solution and reveals that helical folding is substantially reduced in oligomers containing a guanidinium group.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Postelongation Strategy for the Introduction of Guanidinium Units in the Main Chain of Helical Oligourea Foldamers

et al. 2018

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“…3-((2,4,4-trimetilpentán-2-il) Fenil-3-((2,4,4-trimetilpentán-2-il) 3-((2,4,4-trimetilpentán-2-il) 2-(3,4-Difluorfenil)-3-((2,4,4-trimetilpentán-2-il) Fluor-3-(trifluormetil)fenil)-3-((2,4,4-trimetilpentán-2-il) 2-(4-fluor-3-(trifluormetil) 2-(2,4,6-trimetoxifenil)-1H-imidazo[1,2-b 16,3, 30,0, 54,6, 65,1, 115,4, 122,8, 126,8, 126,9, 127,6, 128,4, 128,7, 128,9, 136,9, 137,8, 145,1; MS (ESI): 320,1 [M+H] + . 2-(1-Fenilprop-1-én-2-il)-3-((2,4,4-trimetilpentán-2-il) 16,7,28,9,31,3,31,7,55,3,58,6,65,0,115,4,122,5,126,7,126,9,127,8,128,4,128,9,129,3,136,9,137,7,145 Butil)-3-((2,4,4-trimetilpentán-2-il) Etil-6-metil-2-(1-fenilprop-1-én-2-il)-3-((...…”

Section: Scheme 66unclassified

Izocianid alapú egyedényes módszerek kidolgozása

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A Unified Approach to Access N‐Acyl Sulfonamide Tethered Peptide Conjugates

et al. 2019

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Herein we demonstrate a chemoselective reaction of Nβ‐protected amino alkyl sulfonyl azides with in situ generated Nα‐protected amino acid selenocarboxylates via step wise intramolecular cyclization followed by decomposition to obtain N‐acyl sulfonamide tethered peptidyl conjugates. The protocol offers the synthesis of orthogonally protected N‐acyl sulfonamide tethered peptidomimetics under simple and mild reaction conditions employing commercially available amino acids in presence of NaBH2Se3 as a selenating agent. Also, the synthesis of N‐acyl sulfonamide tethered amino acid and aryl conjugates were accomplished as an extension of the above strategy.

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Synthesis of N-urethane protected amino alkyl (S-methyl)-isothiouronium compounds and carbodiimide tethered peptidomimetics: an application for guanidino and substituted guanidino peptidomimetics synthesis

Cited by 6 publications

References 51 publications

Postelongation Strategy for the Introduction of Guanidinium Units in the Main Chain of Helical Oligourea Foldamers

Postelongation Strategy for the Introduction of Guanidinium Units in the Main Chain of Helical Oligourea Foldamers

Izocianid alapú egyedényes módszerek kidolgozása

A Unified Approach to Access N‐Acyl Sulfonamide Tethered Peptide Conjugates

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