Total Synthesis of Azumamide E and Sugar Amino Acid-Containing Analogue

Chandrasekhar, Srivari; Chennamaneni, Lohitha Rao; Seenaiah, Mallikanti; Jagadeesh, B.; Manjeera, Dharani; Sarkar, Arpita; Bhadra, Manika Pal

doi:10.1021/jo8020264

Cited by 31 publications

(21 citation statements)

References 27 publications

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“…Azumamide E, one of the most potent of the azumamides, also showed roughly 100-fold selectivity for class I over class II HDACs (HDAC1–3, IC 50 = 50–100 nM versus HDAC4–7, 9, IC 50 = 9.7–28 μM) [94]. Chandrasekhar et al [95] reported the total synthesis of azumamide E and sugar amino acid-containing analog (azumamide E-SAA) 3 . A near total inhibition of HDAC activity in a cell-free system was achieved by 20 μM of compound 3 .…”

Section: Review Of Macrocyclic Hdacimentioning

confidence: 99%

Macrocyclic Histone Deacetylase Inhibitors

Mwakwari¹,

Patil²,

Guerrant³

et al. 2010

CTMC

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Histone deacetylase inhibitors (HDACi) are an emerging class of novel anti-cancer drugs that cause growth arrest, differentiation, and apoptosis of tumor cells. In addition, they have shown promise as anti-parasitic, anti-neurodegenerative, anti-rheumatologic and immunosuppressant agents. To date, several structurally distinct small molecule HDACi have been reported including aryl hydroxamates, benzamides, short-chain fatty acids, electrophilic ketones, and macrocyclic peptides. Macrocyclic HDACi possess the most complex cap-groups which interact with HDAC enzyme’s outer rim and have demonstrated excellent HDAC inhibition potency and isoform selectivity. This review focuses on the recent progress and current state of macrocyclic HDACi.

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Section: Review Of Macrocyclic Hdacimentioning

confidence: 99%

Macrocyclic Histone Deacetylase Inhibitors

Mwakwari¹,

Patil²,

Guerrant³

et al. 2010

CTMC

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“…1) and their homooligomers are part of several bioactive macromolecules (Gruner et al 2001(Gruner et al , 2002aChandrasekhar et al 2009). Among them, H-RibAFU(ip)-OH, (1a) (Gruner et al 2002b) and its xylo epimer H-XylAFU(ip)-OH (2a) (Chandrasekhar et al 2004) as hydrophilic analogs of cisand trans-ACPC monomers were incorporated into β-peptidic heterooligomers.…”

Section: Introductionmentioning

confidence: 99%

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

et al. 2016

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We report the solid phase synthesis of -GG-X-GG-type α/β-carbopeptoids incorporating RibAFU(ip) (1a, tX) or XylAFU(ip) (2a, cX) sugar amino acids. Though coupling efficacy is moderate, both the lengthier synthetic route using Fmoc deriva-tive (e.g., Fmoc-RibAFU(ip)-OH) and the azido deriva-tive (e.g., N 3 -RibAFU(ip)-OH) via Staudinger reaction with nBu 3 P can be successfully applied. Both X-ray dif-fraction, 1 H-and 31 P-NMR, and theoretical (QM) data support and explain why the application of Ph 3 P as Staudinger reagent is "ineffective" in the case of a cis stereoisomer, if cX is attached to the preceding residue with a peptide (-CONH-) bond. The failure of the poly-peptide chain elongation with N 3 -cX originates from the "coincidence" of a steric crowdedness and an electronic effect disabling the mandatory nucleophilic attack dur-ing the hydrolysis of a quasi penta-coordinated triph-enylphosphinimine. Nevertheless, the synthesis of the above α/β-chimera peptides as completed now by a new pathway via 1,2-O-isopropylidene-3-azido-3-deoxy-ribo-and -xylo-furanuronic acid (H-RibAFU(ip)-OH 1a and H-XylAFU(ip)-OH 2a) coupled with N-protected α-amino acids on solid phase could serve as useful examples and starting points of further synthetic efforts.

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“…16,17 The unusual norbornane amino acid was synthesized as reported in the literature using commercially available norbornene. [16][17][18][19][20] The synthesis was performed in two pathways: (i) synthesis of dimers and tetramer (ii) synthesis of hexamer followed by Yamaguchi macrocyclization. [21][22][23] (S)-Phenylalanine amine salt (1) in DCM solution is neutralized with TEA at 0°C to get (S)-methyl 2-amino-3-phenyl propionate (2).…”

Section: Results and Discussion: Chemistrymentioning

confidence: 99%

Synthesis of novel (±)-cis-exo-norbornane amino acid containing cyclic hexapeptide: Analogue of Dolastatin 16

Guggilapu

2015

Proceedings of the 19th International Electronic Conference on Synthetic Organic Chemistry

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Novel cyclohexapeptide has been synthesized by replacing the unusual amino acids (dolaphenvaline and dolaphenleuine) of dolastatin 16 with (±)-cis-exo-norbornane and phenyl alanine amino acids. Novel cyclic hexapeptide alongwith dimers, tetramers composed of alternating L-proline subunin have been synthesized in solution phase and well characterized. KEYWORDSDolastatin 16, exo-norbornane amino acid, peptide synthesis, cyclic hexapeptide.

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Total Synthesis of Azumamide E and Sugar Amino Acid-Containing Analogue

Cited by 31 publications

References 27 publications

Macrocyclic Histone Deacetylase Inhibitors

Macrocyclic Histone Deacetylase Inhibitors

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

<strong>Synthesis of novel </strong>(±)-<strong><em>cis-exo</em></strong><strong>-norbornane amino acid containing cyclic hexapeptide: Analogue of Dolastatin 16 </strong>

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Total Synthesis of Azumamide E and Sugar Amino Acid-Containing Analogue

Cited by 31 publications

References 27 publications

Macrocyclic Histone Deacetylase Inhibitors

Macrocyclic Histone Deacetylase Inhibitors

Origin of problems related to Staudinger reduction in carbopeptoid syntheses

<strong>Synthesis of novel </strong>(&plusmn;)-<strong><em>cis-exo</em></strong><strong>-norbornane amino acid containing cyclic hexapeptide: Analogue of Dolastatin 16 </strong>

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<strong>Synthesis of novel </strong>(±)-<strong><em>cis-exo</em></strong><strong>-norbornane amino acid containing cyclic hexapeptide: Analogue of Dolastatin 16 </strong>