Isolation and Crystal Structure of Stylopeptide 1, A New Marine Porifera Cycloheptapeptide

Pettit, George R.; Srirangam, Jayaram K.; Herald, Delbert L.; Xu, Jun‐Ping; Boyd, Michael R.; Cichacz, Zbigniew A.; Kamano, Yoshiaki; Schmidt, Jean M.; Erickson, Karen L.

doi:10.1021/jo00130a027

Cited by 53 publications

(49 citation statements)

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“…7 Hz clearly suggests an equilibrium of several side-chain conformers. Since during the simulation only one rotamer occurs, the Hpro-s-C(p)) = 2.2 Hz).…”

Section: Results Andmentioning

confidence: 94%

“…To our knowledge, phakellistatin 1 (cycle(-Pro '-Ile2-Pro3-Ile4-Phe'-Pro6-Tyr7)) [32] is the only known structure with two cis amide bonds in the p turns about Ile2/Pro3 and Phe'/Pro6. There have been few examples for transltrans configuration in the , 8 turns: pseudostellarin D (cycle(-G1y'-Tyr2-Cly3-Pro4-Leu5-Ile6-Leu7)) [16] shows a PI1 turn about Leu7 and Gly' and a PI turn about Pro4 and Leu', whereas yunnanin A (cyclo(-G1y'-Tyr2-G1y3-Gly4-Pro5-Phe6-Pro7)) [33] [34], hymenamide B-F [35], stylopeptide [7], isophakellistatin 3 [36], stylostatin 1 [S] [28], and axinastatin 1 [25], form the cis amide bond at a proline residue. For all these cyclic heptapeptides, the overall backbone conformation is similar to the structures of axinastatins 2 -4, investigated here.…”

Section: Axinastatin 4 (3) In Dmso Axinastatin 4 (3)mentioning

confidence: 99%

“…~7 1 . 7. Schematic description of the extension of the Dunitz-Waser concept to peptides Fig. 8,a shows the side view of the overall shape of the bent backbone of axinastatin 2 (1) in DMSO.…”

Section: Axinastatin 4 (3) In Dmso Axinastatin 4 (3)mentioning

confidence: 99%

“…During the last years, many cyclic peptides with cancer cell growth inhibitory properties, such as stylopeptide [7], stylostatin 1 [S], hymenistatin 1 [9], and axinastatin 1 [lo], were obtained from marine sources. Cyclic compounds have a restricted conformational space.…”

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confidence: 99%

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Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential

Mechnich¹,

Messier²,

Kessler³

et al. 1997

Helvetica Chimica Acta

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Dedicated to Ernst B q e r on the occasion of his 70th birthday (24.11.97) The conformational analysis of naturally occurring cytostatic cyclic: heptapeptides axinastatin 2, 3, and 4 was carried out by two-dimensional NMR spectroscopy in combination with distance-geometry (DG) and molecular- In all peptides, a bifurcated H-bond occurs between residue 4 CO and the amide protons of residue 1 and 7. For axinastatin 2 and 3, an Asn 1, turn was found about Asn' and Pro'. We compared these structures with conformations of cyclic heptapeptides obtained by X-ray and NMR studies. A P-bulge motif with two turns and one bifurcated H-bond is found as the dominating backbone conformation of cyclic all-L-heptapeptides. Axinastatin 2, 3, and 4 can be characterized by six fruns and one cis amide bond resulting in a PI/PVI(a)-turn motif, a conformation found for many cyclic heptapeptides. Detailed biological tests of the synthetic compounds in different human cancer cell lines indicates these axinastatins to be inactive or of low activity.

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“…7 Hz clearly suggests an equilibrium of several side-chain conformers. Since during the simulation only one rotamer occurs, the Hpro-s-C(p)) = 2.2 Hz).…”

Section: Results Andmentioning

confidence: 94%

Section: Axinastatin 4 (3) In Dmso Axinastatin 4 (3)mentioning

confidence: 99%

Section: Axinastatin 4 (3) In Dmso Axinastatin 4 (3)mentioning

confidence: 99%

mentioning

confidence: 99%

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Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential

Mechnich¹,

Messier²,

Kessler³

et al. 1997

Helvetica Chimica Acta

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“…The acid 7a was extracted into EtOAc and washed with a 10% solution of citric acid followed by H2O before being dried over MgSO4. Volatiles were removed in vacuo, and the resulting oil was purified by flash chromatography (CH2Cl2/ MeOH, 19:1) to yield a white solid (2.54 g, 90%): mp 28 N-[4-(5-Oxy-(trimethylsilylethylvalerate))benzyl]-Lisoleucine Allyl Ester (5b). The aldehyde 4 (16.2 g, 50.2 mmol), isoleucine allyl ester (20.5, 100 mmol), and excess MgSO4 (∼40 g) were stirred in CH2Cl2 (75 mL) at rt for 3 h. Solids were filtered, and volatiles were removed in vacuo to yield the crude imine as a yellow oil.…”

Section: Boc-l-pro-[n-(4-(5-oxyvaleric Acid)benzyl)]-l-phenylalanine mentioning

confidence: 99%

A Backbone Linker for BOC-Based Peptide Synthesis and On-Resin Cyclization: Synthesis of Stylostatin 1^,

et al. 1999

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We have developed a new 4-alkoxybenzyl-derived linker that anchors the C-terminal amino acid to the resin through the alpha-nitrogen atom. The linker allows BOC solid-phase peptide assembly and peptide cleavage using standard HF protocols. This linking strategy provides a versatile on-resin route to cyclic peptides and avoids the diketopiperazine formation that is prominent when using FMOC chemistry on backbone linkers. The linker was prepared by forming the aryl ether from 4-hydroxybenzaldehyde and bromovaleric acid. Subsequent reductive amination of the aldehyde with an allyl-protected amino acid ester and acylation of the resulting secondary amine provided the tertiary amide. After linking the amide to the resin, standard BOC SPPS, followed by allyl deprotection, cyclization, and HF cleavage gave cyclic peptides in high purity. To exemplify the strategy, the cytotoxic heptapeptide, stylostatin 1, was synthesized from two linear precursors. For comparison purposes, the yields of the on-resin and solution-phase cyclization were determined and found to be dependent upon the linear precursor. This linker technology provides new solid-phase avenues in accessing libraries of cyclic peptides.

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Porifera (Sponges)–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Secondary Metabolites of Hadromerida and Chondrosida Perforating Power of Clionaidae lyso ‐Phospholipids and Sulfated Sphingosines of Spirastrella abata Brominated Acetylenic Derivatives of Diplastrella Cyclic Peroxides Terpenes Unconventional Sterols Macrolactones: Latrunculins and Spongistatins Atypical Glycosides of Latrunculia corticata Other Nitrogen‐Free Toxins Peptides and Depsipeptides Pyrrole Derivatives and other Nitrogen‐Containing Heterocycles Atypical Nucleosides Secondary Metabolites of Lithistida Particular Characteristics of Lithistid Sponges Unusual Halogenated Fatty Acids Nitrogen‐Containing Sesquiterpenes of Theonella Specific Glycolipids of Theonella swinhoei, Discodermia calyx and D. dissoluta Long‐Chain Polyacetylenic Derivatives of Theonella sp 3β‐Methoxysterols of Jereicopsis graphidiophora 4‐Methylene Sterols and Sterones of Theonella Macrolides Examples of Acetogenins: Discodermolide, Calyculins, and Onnamides Linear Amides and Peptides Mono‐ and Bicyclic Peptides Symbiotic Origin of Some Polypeptides Cyclic and Linear Depsipeptides Atypical Nitrogenous Derivatives Secondary Metabolites of Spirophorida Atypical Sterols of Cinachyra, Microscleroderma , and Scleritoderma Cinachyrolide A, Enigmazole A Microsclerodermins and Aciculitins Examples of Atypical Derivatives of Some Sponges of the Tetillidae Secondary Metabolites of Agelasida Sterols Diterpenes and Carotenoids Gracilioethers of Agelas gracilis Merosesquiterpenes and Nitrogen‐Containing Meroditerpenes Galactosylceramides and Glycolipids Oroidin and Related C 11 N 5 Bromopyrrole Alkaloids Oroidin Series Agelastatin A Series Other Series Pyrrole‐2‐carboxylic Acid Derivatives Other Examples of Nitrogen‐Containing Heterocycles Betaines Secondary Metabolites of Halichondrida A‐ nor ‐Steroids and Other Nonconventional Sterols Conventional Terpenes Nitrogen‐Containing Terpenes: Isonitriles and Related Derivatives Other Terpenes Long‐Chain Linear Polyamines and α,ω‐bis‐isothiocyanates Polyethers: Halichondrins, Okadaic, and Glycookadaic Acids Various Lipids Linear Peptides of the Genera Auletta and Cymbastela Depsipeptides and Cyclic Peptides Unusual Amino Acids and Betaines Pyrrole, Imidazole, Pyridine, Isoquinoline, and Indole Derivatives Pyrrole Derivatives Imidazole Derivatives Pyridine and Isoquinoline Derivatives Indole Derivatives Heterocycles Related to the Oroidin Family Atypical Halogenated and Sulfur‐Containing Derivatives

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Isolation and Crystal Structure of Stylopeptide 1, A New Marine Porifera Cycloheptapeptide

Cited by 53 publications

References 0 publications

Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential

Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential

A Backbone Linker for BOC-Based Peptide Synthesis and On-Resin Cyclization: Synthesis of Stylostatin 1^,

Porifera (Sponges)–2

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Isolation and Crystal Structure of Stylopeptide 1, A New Marine Porifera Cycloheptapeptide

Cited by 53 publications

References 0 publications

Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential

Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential

A Backbone Linker for BOC-Based Peptide Synthesis and On-Resin Cyclization: Synthesis of Stylostatin 1,

Porifera (Sponges)–2

Contact Info

Product

Resources

About

A Backbone Linker for BOC-Based Peptide Synthesis and On-Resin Cyclization: Synthesis of Stylostatin 1^,