The Cleavage of Ethers by Triphenyldibromophosphorane

Anderson, Arthur G.; Freenor, Francis J.

doi:10.1021/ja01076a084

Cited by 38 publications

(16 citation statements)

References 2 publications

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“…3. Acylation of H-Pro-OBzl (6) with Boc-Gln-OSu (7) yielded the dipeptide Boc-Gln-Pro-OBzl (X), which was selectively deprotected by trifluoroacetic acid and allowed to react with Z-Gly-OSu (5). The resulting protected tripeptide 2-Cly-Gln-Pro-OBzl (XI) was converted into the corresponding hydrazide and reacted, by the azide procedure, with H-Arg (N02)-NHGlc (3).…”

Section: -Butyloxycarbonyl-hydrazidementioning

confidence: 99%

Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives

Rocchi

Biondi

Cavaggion

et al. 1987

International Journal of Peptide and Protein Research

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Synthesis of some modified rigins is described in which either D‐gluconic acid or 2‐amino‐2‐deoxy‐β‐D‐glucopyranose have been linked to the parent molecule through amide bonds involving the α‐amino function, α‐carboxyl function or the γ‐amide function of glutamine in position 2. Glu2‐rigin and D‐gluconyl‐Glu2‐rigin have also been synthesized. Binding and phagocytosis assays have been carried out on the rigin derivatives and on some glycosylated tuftsin derivatives as well. Of all the tested peptides only rigin enhanced the phagocytic capacity of mouse peritoneal macrophages to the same extent as tuftsin. The peptides H‐Thr‐Lys‐Pro‐Arg‐NH‐Glc and Nα‐gluconyl‐Gly‐Glu‐Pro‐Arg‐OH slightly enhanced phagocytosis. H‐Thr[(α + β)‐O‐glucosyl]‐Lys‐Pro‐Arg‐OH was found to displace 3H‐tuftsin even better than tuftsin but lacked the ability to stimulate phagocytosis.

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Section: -Butyloxycarbonyl-hydrazidementioning

confidence: 99%

Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives

Rocchi

Biondi

Cavaggion

et al. 1987

International Journal of Peptide and Protein Research

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“…The mixture was stirred at 0' for 1 h and at room temperature for 12 h. The dicylohexylurea was filtered and the organic solution was washed with 5% NaHC03, water, dried over Na2S04 and evaporated to dryness, giving 16.0g (98%) of uncrystallizable oil. 16.0 g (33.0 mmol) BOC-Val-Pro-Gly-ONp were dissolved in 98% HCOOH (184mL) and the solution was kept at room temperature for 3 h. After evaporation to dryness, the residue was precipitated from ethanol-diethyl ether giving 5.0g crude product (36%), m.p. 159-161°, which was used on the polycondensation step without further purification.…”

Section: Boc-val-pro-cly-onpmentioning

confidence: 99%

Conformational studies on polypeptide models of collagen. Poly(Gly‐Pro‐Val), poly(Gly‐Pro‐Met), poly(Gly‐Val‐Pro) and poly(Gly‐Met‐Pro)

Guantieri

Tamburro

Cabrol

et al. 1987

International Journal of Peptide and Protein Research

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The title polytripeptides were synthesized and studied experimentally, by circular dichroism, and theoretically, by quantum mechanical methods. With the exception of poly(Gly‐Pro‐Val), which was found to be essentially structureless in solution, the other polymers adopt folded conformations, most probably of type II β‐bends. Conclusions from theoretical studies were generally in agreement with the experimental results. In particular, it is noteworthy that the optimized (φ, ø) maps for poly(Gly‐Pro‐Met) showed the absolute minimum (φ = 60°, ø = 0°) located inside the βII bend space.

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“…The by-as an oil, which could be crystallized Acylation of the dipeptide ester 17 with the azide of 10 led to the protected tripeptide ester 18, which separated from methanol in beautiful needles. The free ester (19), also crystalline, was acylated with the azide derived from the known (1 3 ) hydrazide (20). The fully protected crystalline pentapeptide ester was purified by recrystallization from methanol.…”

Section: Pro-nh-nh-boc (A')mentioning

confidence: 99%

“…The ester was acylated with the azide derived from 32, to yield the neutral dipeptide derivative 33, which in turn was deprotected at the 01 position to give 35. This zwitterionic compound was treated with tritylglycine succinimidyl ester (18,19) to give 37 in an unexpectedly facile reaction. Compound 37 was utilised in two ways.…”

Section: Figure 5bmentioning

confidence: 99%

Semisynthesis of the native sequence of horse heart cytochrome c‐(66–104)‐nonatriacontapeptide

Boon

Mous

Kortenaar

et al. 1986

International Journal of Peptide and Protein Research

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The syntheses of some derivatives of horse cytochrome c‐(66–79)‐tetradeca‐peptide are presented. The syntheses are so designed that analogues of this phylogenetically well preserved sequence can be obtained also. The compounds were intended as synthons for the semisynthesis of 65‐homoserine‐cytochrome c, which we described earlier. A requisite for this project was the C‐terminal tetracosapeptide fragment of the protein, accessible through degradation of cytochrome c with cyanogen bromide. The five e amino groups in this compound are reversibly protected with the 2‐(methylsulfonyl)ethyloxycarbonyl function, which is resistant to acid and causes little impairment of solubility. The condensation of the fragments leading to the native sequence of horse cytochrome c‐(66–104)‐nonatriacontapeptide is presented also. The syntheses were performed using the solution strategy. Some unexpected ring closing reactions involving tyrosine and tert.‐butyl prolylasparaginylcarbazate, are described.

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The Cleavage of Ethers by Triphenyldibromophosphorane

Cited by 38 publications

References 2 publications

Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives

Synthesis and biological activity of tuftsin and rigin derivatives containing monosaccharides or monosaccharide derivatives

Conformational studies on polypeptide models of collagen. Poly(Gly‐Pro‐Val), poly(Gly‐Pro‐Met), poly(Gly‐Val‐Pro) and poly(Gly‐Met‐Pro)

Semisynthesis of the native sequence of horse heart cytochrome c‐(66–104)‐nonatriacontapeptide

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