New syntheses of α-amino acids based on n-acylimino acetates

Bretschneider, Till; Miltz, Wolfgang; Münster, Peter; Steglich, Wölfgang

doi:10.1016/s0040-4020(01)86046-4

Cited by 87 publications

(22 citation statements)

References 23 publications

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“…The product was obtained in quantitative yield (3.00g, 97%) and used without further purification. As previously reported in other methods, [20][21][22][23] the reaction time, temperature, the intensity of UV light and the species of brominating agents were the key factors for this reaction. The other glycine template, CBZ-Gly(Br)-OMe (N-(Benzyloxycarbonyl)-α-bromoglycine methylester), was acquired with the total yield of 70% according to the previous reported synthetic pathway.…”

Section: Methodssupporting

confidence: 70%

“…To demonstrate the application of the final product for molecular imaging, the DEVD-aminoDOTA-Tm 3+ complex 11 was tested for the PARAmagnetic Chemical Exchange Saturation Transfer (PARACEST) effect (Fig 2). 23 Selective radio frequency irradiation at -51ppm caused a saturation of the amide proton proximal to Tm 3+ in 11, and subsequent chemical exchange of this proton with water transferred the saturation to the water, which decreased the MR water signal. This PARACEST effect of 11 occurs at the same chemical shift frequency reported for the PARACEST effect of a similar compound, DOTAMGly-Tm 3+ .…”

Section: Discussionmentioning

confidence: 99%

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Novel Molecular Imaging Agents to Detect Biomarkers of Metastatic Breast Cancer

Pagel¹

2006

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Public reporting burden for this collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing this collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden to Department of Defense, Washington Headquarters Services, Directorate for Information Operations and Reports (0704-0188), 1215 Jefferson Davis Highway, Suite 1204, Arlington, VA 22202-4302. Respondents should be aware that notwithstanding any other provision of law, no person shall be subject to any penalty for failing to comply with a collection of information if it does not display a currently valid OMB control number. PLEASE DO NOT RETURN YOUR FORM TO THE ABOVE ADDRESS. (From -To) We propose to develop novel molecular imaging agents to detect enzyme biomarkers of metastatic breast cancer. These imaging agents are detected using magnetic resonance imaging (MRI) only if they encounter enzymes that are present in metastatic breast tumors. Unlike standard MRI agents, these novel agents are detected by a unique mechanism that allows for evaluations of multiple enzymes during the same MRI experiment. The ability to simultaneously detect multiple enzyme biomarkers within a single MRI scan session will reduce scan times and patient discomfort. The unique detection mechanism employed by these MRI agents will take full advantage of new high-field clinical MRI scanners; this is in contrast to standard MRI agents, which show only limited improvements at high magnetic fields. We will generate these novel agents using standard chemistry protocols. We'll optimize our MRI methods to detect enzyme biomarkers with these agents, and we will use well-established fluorescence imaging methods to validate our results. Finally, we'll apply these agents to detect the enzyme biomarkers within metatstatic breast tumor cells grown in mice. As a long-term goal, these novel molecular imaging agents will be further developed for clinical assessments of metastatic breast cancer. REPORT DATE (DD-MM-YYYY) 01-01-2006 REPORT TYPE Final DATES COVERED SUBJECT TERMSPerformance of research to accomplish goals listed in the abstract. IntroductionWe have developed novel molecular imaging agents that detect matrix metaloprotenase enzyme MMP-2 and MMP-9 that are confirmed biomarkers of metastatic breast cancer. These "smart" imaging agents are activated by MMP-2 or MMP-9 enzymatic activity for detection by magnetic resonance imaging (MRI). Unlike standard MRI agents, these novel molecular imaging agents have unique MR frequencies, and we have shown that multiple agents can be simultaneously used to assess multiple biomarkers. We have also shown that these new agents detect only the active forms of these biomarkers, which is critical for proper evaluation of metastatic breast cancer. We have developed new methodologies...

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Section: Methodssupporting

confidence: 70%

Section: Discussionmentioning

confidence: 99%

Novel Molecular Imaging Agents to Detect Biomarkers of Metastatic Breast Cancer

Pagel¹

2006

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“…Effective monobromination of each of two or more methyl group attached to a benzenoid ring was reported in a project aimed for the preparation of artificial receptors. 74 The trimethyl substrates (36) and (37) and the dimethyl substrate reported to provide a good test of the strength of the procedure because of the opportunities for polybromination. 74 The procedure developed reported to give acceptable yields of the desired product (36)-(38) ( Table 3).…”

Section: 8: Solvents For Nbs Brominationmentioning

confidence: 99%

Regioselectivity in free radical bromination of unsymmetrical dimethylated pyridines

Thapa

Brown

Balestri

et al. 2014

Tetrahedron Letters

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“…The discussed ylides are widely used for the synthesis of bicyclic β-lactam antibiotics. One of the earliest methods of synthesizing them, described by Woodward, consists in the treatment of the corresponding β-lactams 14 with glyoxylic acid esters [17][18][19][20][21][22] or their hemiacetals, 8,23,24 which yields the corresponding α-hydroxyglycine derivatives 15. The latter compounds react with thionyl chloride, followed by their reaction with triphenylphosphine in the presence of bases.…”

Section: Figurementioning

confidence: 99%

α-Amino acid derivatives with a Cα-P bond in organic synthesis

Mazurkiewicz¹,

Kuźnik²,

Grymel³

et al. 2007

Arkivoc

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α-Amino acid derivatives with a C α -P bond have been used for a wide range of chemical transformations, including synthesis of many kinds of bioactive compounds, e.g. nonproteinogenic α-amino acids, α,β-dehydro-α-amino acids, dehydropeptides, β-lactam antibiotics and glycopeptides. The present review is focused on methods of synthesis of the title compounds, their properties and application in organic synthesis.

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New syntheses of α-amino acids based on n-acylimino acetates

Cited by 87 publications

References 23 publications

Novel Molecular Imaging Agents to Detect Biomarkers of Metastatic Breast Cancer

Novel Molecular Imaging Agents to Detect Biomarkers of Metastatic Breast Cancer

Regioselectivity in free radical bromination of unsymmetrical dimethylated pyridines

α-Amino acid derivatives with a Cα-P bond in organic synthesis

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