- High-efficiency preparation method of D-dencichine
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The invention relates to a high-efficiency synthesis method of a hemostasis compound D-dencichine, comprising the following steps: firstly enabling D-serine to react with di-tert-butyl dicarbonate ester to generate Boc-D-serine, then generating Gabriel reaction with hydroxy of methylsulfonyl chloride activated Boc-D--serine to obtain N-alpha-Boc-D-alpha, beta-diaminopro, finally condensing with oxalate mono-methyl ester sylvite then performing hydrolytic acidification to obtain a dencichine crude product, and purifying to obtain a dencichine competitive product, with the product content reaching more than 99.8%. Compared with existing D-dencichine synthesis methods, the reaction condition is more mild, the operation is simple and convenient, the material cost is relatively low, and the hemostasis compound D-dencichine is environment-friendly, is suitable for industrial production, and solves the problem of resource for later development of clinical trial of D-dencichine.
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- New 2,3-diaminopropionic acid inhibitors of AGE and ALE formation
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Novel 2,3-diaminopropionic acid-based molecules were synthesised and tested successfully as glyoxal/methylglyoxal scavengers and as AGE inhibitors. Addition of an 8-hydroxyquinoline moiety led to an increase of the overall activity. The compounds tested in this study were also proved to be efficient in trapping ALE precursor malondialdehyde. The Royal Society of Chemistry 2013.
- Audic, Nicolas,Potier, Guy,Sasaki, N. André
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p. 773 - 780
(2013/03/13)
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- Aminomethylene peptide nucleic acid (am -PNA): Synthesis, regio-/stereospecific DNA binding, and differential cell uptake of (α/γ, R / S) am- PNA analogues
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Inherently chiral, cationic am-PNAs having pendant aminomethylene groups at α(R/S) or γ(S) sites on PNA backbone have been synthesized. The modified PNAs are shown to stabilize duplexes with complementary cDNA in a regio- and stereo-preferred manner with γ(S)-am PNA superior to α(R/S)-am PNAs and α(R)-am PNA better than the α(S) isomer. The enhanced stabilization of am-PNA:DNA duplexes is accompanied by a greater discrimination of mismatched bases. This seems to be a combined result of both electrostatic interactions and conformational preorganization of backbone favoring the cDNA binding. The am-PNAs are demonstrated to effectively traverse the cell membrane, localize in the nucleus of HeLa cells, and exhibit low toxicity to cells.
- Mitra, Roopa,Ganesh, Krishna N.
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experimental part
p. 5696 - 5704
(2012/08/07)
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- PNAs grafted with (α/γ, R/S)-aminomethylene pendants: Regio and stereo specific effects on DNA binding and improved cell uptake
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PNAs grafted with cationic aminomethylene (am) pendants on the backbone at the glycyl (α) or ethylenediamine (γ) segments show regio (α/γ) and stereochemistry (R/S) dependent binding with complementary DNA. These are efficiently taken up by cells, with γ(S-am) aeg-PNA being the best in all properties.
- Mitra, Roopa,Ganesh
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supporting information; experimental part
p. 1198 - 1200
(2011/03/20)
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- Novel inhibitors of procollagen C-terminal proteinase. Part 1: Diamino acid hydroxamates
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The parallel synthesis of novel inhibitors of procollagen C-terminal proteinase is described. The synthetic strategy allowed for the facile synthesis of a large number of side-chain diversified diamino acid hydroxamates, of which the D-diaminopropionic acid derivatives were shown to be single digit nanomolar PCP inhibitors.
- Delaet,Robinson,Wilson,Sullivan,Bradley,Dankwardt,Martin,Van Wart,Walker
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p. 2101 - 2104
(2007/10/03)
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- The design, synthesis, and biological evaluation of analogues of the serine-threonine protein phosphatase 1 and 2A selective inhibitor microcystin LA: Rational modifications imparting PP1 selectivity
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Based on the results from previously reported molecular modeling analyses of the interactions between the inhibitor microcystin and the serine-threonine protein phosphatases 1 and 2A, we have designed analogues of microcystin LA with structural modifications intended to impart PP1 selectivity. The synthesis of several first generation analogues followed by inhibition assays revealed that all three are PP1-selective, as predicted. Although the observed selectivities are modest, one of the designed analogues is more selective for PP1 than any known small molecule inhibitor. Copyright (C) 1999 Elsevier Science Ltd.
- Aggen, James B.,Humphrey, John M.,Gauss, Carla-Maria,Huang, Hsien-Bin,Nairn, Angus C.,Chamberlin, A. Richard
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p. 543 - 564
(2007/10/03)
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- Studies related to the absolute configuration of cyclocinamide A: Total synthesis of 4(R),11(R)-cyclocinamide A
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Coupling of the fluorenylmethyl ester 3 (R = Fm) of (S)-5- bromotryptophan with N(α)-BOC-(S)-asn-O-benzoyl-(R)-ise 9 gave rise to tripeptide 10. Cleavage of the BOC group in 10 followed by coupling with N(α)-BOC-N(β)-Fmoc-(R)-2,3-diaminopropanoic acid afforded tetrapeptide 11 which was transformed into cyclic peptide 12. Cleavage of the BOC in 12 followed by coupling with the glycine derived side chain 14 gave rise, after removal of the benzoyl group to 4(R),11(R)-cyclocinamide A(2) which was not identical to natural cyclocinamide A(1), suggesting that 1 possesses the 4(S),7(S),11(S),14(S) configuration.
- Grieco, Paul A.,Reilly, Michael
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p. 8925 - 8928
(2007/10/03)
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- Synthesis of [L-3-deoxymimosine4]-angiotensin I as an approach to the preparation of selective protein-tyrosine kinase (PTK) inhibitors
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tert-Boc-L-3-Deoxymimosine (13) and tert-Boc-D-Deoxymimosine (16) were prepared in two steps from tert-Boc-L-asparagine and tert-Boc-D-asparagine, respectively. Both 13 and 16 were determined to be optically pure by derivatization with Marphey's reagent. Activation and coupling of 16 to L-isoleucine methyl ester resulted in a diastereomeric mixture of products containing 96% of the DL diastereomer and 4% of the LL diastereomer. [L-3-Deoxymimosine4]-angiotensin I was synthesized from 13 as an approach to the design and synthesis of selective protein-tyrosine kinase (PTK) inhibitors.
- Lee, Eung-Seok,Jurayj, Jurjus,Cushman, Mark
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p. 9873 - 9882
(2007/10/02)
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- QUANTITATIVE SYNTHESIS OF L OR D N2-TERTBUTOXYCARBONYL-2,3-DIAMINOPROPANOIC ACID FROM PROTECTED L OR D SERINE-β-LACTONE
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The reaction of ammonia on protected L or D serine-β-lactone was reinvestigated.An easy synthesis of N2-tertbutoxycarbonyl-L-2,3-diaminopropanoic acid (and D enantiomer), an important precursor of several antibiotics is proposed.
- Kucharczyk, N.,Badet, B.,Goffic, F. Le
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p. 1603 - 1610
(2007/10/02)
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