869116-13-2Relevant academic research and scientific papers
Synthesis of L-[5-11C]Leucine and L-α-[5-11C]Methylleucine via Pd0-mediated 11C-Methylation and Microfluidic Hydrogenation: Potentiality of Leucine PET Probes for Tumor Imaging
Takatani, Shuhei,Tahara, Tsuyoshi,Tsuji, Mieko,Ozaki, Daiki,Shibata, Nina,Hashizume, Yoshinobu,Suzuki, Masaaki,Onoe, Hirotaka,Watanabe, Yasuyoshi,Doi, Hisashi
, p. 3271 - 3279 (2021)
The efficient synthesis of L-[5-11C]leucine and L-α-[5-11C]methylleucine has been investigated using a continuous two-step sequence of rapid reactions consisting of Pd0-mediated 11C-methylation and microfluidic hydrogenation. The synthesis of L-[5-11C]leucine and L-α-[5-11C]methylleucine was accomplished within 40 min with a decay-corrected radiochemical yield of 15–38 % based on [11C]CH3I, radiochemical purity of 95–99 %, and chemical purity of 95–99 %. The Pd impurities in the injectable solution measured using inductively coupled plasma mass spectrometry met the international criteria for human use. Positron emission tomography scanning after an intravenous injection of L-[5-11C]leucine or L-α-[5-11C]methyl leucine in A431 tumor-bearing mice was performed. As a result, L-α-[5-11C]methylleucine was found to be a potentially useful probe for visualizing the tumor. Tissue distribution analysis showed that the accumulation value of L-α-[5-11C]methylleucine in tumor tissue was high [12±3% injected dose/g tissue (%ID/g)].
Synthesis of desmosine-BSA/KLH conjugates via Sonogashira/Negishi cross-coupling reactions
Miyagi, Seiya,Yokoo, Reiko,Tanigawa, Takahiro,Pitna, Dinda B.,Hirose, Mika,Usuki, Toyonobu
, (2022/01/14)
Desmosine is an elastin crosslinking amino acid that is expected to be a useful biomarker of diseases related to elastin degradation including chronic obstructive pulmonary disease (COPD). In this study, conjugates of desmosine and carrier proteins, such
An improved large scale procedure for the preparation of N-Cbz amino acids
Pehere, Ashok D.,Abell, Andrew D.
experimental part, p. 1493 - 1494 (2011/05/16)
A simple and scalable method for the preparation of N-Cbz protected amino acids is presented which uses a mixture of aqueous sodium carbonate and sodium bicarbonate to maintain the appropriate pH during the addition of benzyl chloroformate. The method has been extended to other N-protections and is amenable to large scale preparation of an intermediate toward Zofenopril, an ACE inhibitor.
Cu-catalyzed formation of triazole-linked glycoamino acids and application in chemoenzymatic peptide synthesis
Kuijpers, Brian H. M.,Groothuys, Stan,Hawner, Christine,Dam, Jeroen Ten,Quaedflieg, Peter J. L. M.,Sehoemaker, Hans E.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
, p. 503 - 511 (2013/01/03)
Novel stable triazole-linked glycoamino acids have been prepared, with the heterocyclic moiety being established by efficient Cumediated cycloaddition between the corresponding azido and acetylene moieties. Selected reactions were scaled up and successful
Chemoenzymatic synthesis of triazole-linked glycopeptides
Groothuys, Stan,Kuijpers, Brian H. M.,Quaedflieg, Peter J. L. M.,Roelen, Harlof C. P. F.,Wiertz, Roel W.,Blaauw, Richard H.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
, p. 3146 - 3152 (2008/02/09)
Triazole-linked glycopeptides are prepared by C-terminal elongation of glycoamino acids with proteinogenic amino acids following a chemical or enzymatic coupling protocol. Two orthogonal routes for a chemoenzymatic strategy were explored, involving a click-reaction before amide bond formation or in reverse order. It was found that enzymatic peptide coupling under the influence of alcalase proceeds cleanly and in high yields, while the resulting dipeptides can be efficiently clicked to acetylene- or azide-containing sugars. Georg Thieme Verlag Stuttgart.
