Search results for "solid-phase synthesis"
showing 10 items of 60 documents
Carbohydrate Scaffolds for Combinatorial Syntheses That Allow Selective Deprotection of All Four Positions Independent of the Sequence
2004
Synthesis and biological properties of the seven alanine-modified analogues of the marine cyclopeptide hymenamide C
2002
The synthesis and biological activity of the marine cyclopeptide hymenamide C(1), showing an inhibitory effect on human neutrophil elastase degranulation release, were recently described. Based on this result, it was decided to undertake a systematic structure-activity relationship study of this cyclopeptide, based on the Ala-scan technique, in order to obtain useful information for the rational design of additional analogues. The synthesis and characterization of the seven Ala modified analogues are reported and their biological and pharmacological properties are described.
Cover Picture: Synthesis and Biological Evaluation of a Multiantigenic Tn/TF-Containing Glycopeptide Mimic of the Tumor-Related MUC1 Glycoprotein (Ch…
2006
D-Glucose as a Pentavalent Chiral Scaffold
2003
A novel carbohydrate-based scaffold for combinatorial chemistry has been developed. This scaffold allows the selective attachment of five different side chains, giving rise to products of enormous structural diversity. As a demonstration of its usefulness, a series of model compounds has been prepared in high purity and yield by multistep parallel synthesis on a solid phase. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Combinatorial solid-phase synthesis using D-galactose as a chiral five-dimension-deversity scaffold
1999
Abstract All five hydroxy groups of galactose as the scaffold are used for selective coupling of side chains in a combinatorial methodology by application of a set of orthogonally stable protecting groups in combination with a thioglycoside anchor.
ChemInform Abstract: The Development of Synthetic Antitumor Vaccines from Mucin Glycopeptide Antigens
2013
Synthesis of Biologically Interesting Glycopeptides.
1992
哺乳動物に見い出される大部分のタンパクは糖タンパクである。それらの糖鎖は生物学的選択性、特に膜上での認識過程に重要な働きをしている。全ての糖タンパクは糖鎖とペプチドとの間にグリコシド結合を有している。それゆえに糖ペプチドの化学合成は、立体特異的なグリコシド結合の生成と、グリコシド結合に影響を与えない選択的な保護が要求される。ベンジルグループとそれらの水素添加による脱離法は、これらの要求を満たす。しかしながら、これらの保護法を用いる方法は糖質の水酸基のブロックを必要とするので、ペプチド部分の官能基は撰択的に脱離可能でそしてベンジル基に対して orthogonal に安定なグループで保護されなければならない。この意味においてフルオレニルメトキシカルボニル (Fmoc) 基と、弱塩基、モルフォリンによる脱離と、パラジウム (0) 触媒によるアリル基転移によって脱離可能なアリルオキシカルボニル (Aloc) 基は、糖ペプチド化学においてアミノ基の保護基として有用である事が明らかにされた。同様なパラジウム (0) の化学を用いるアリルエステルと、酸により除去可能なtert-ブチルエステルはカルボキシル基の保護に有用である事が分かった。ベンジル基とアリルエステル (HYCRAM™) を用いる糖ペプチドの固相合成におけるアンカーシステムとして有効に利用される事が示された。
FINDUS: An Open-Source 3D Printable Liquid-Handling Workstation for Laboratory Automation in Life Sciences
2020
3D-printed laboratory devices can enable ambitious research purposes even at a low-budget level. To follow this trend, here we describe the construction, calibration, and usage of the FINDUS (Fully Integrable Noncommercial Dispensing Utility System). We report the successful 3D printing and assembly of a liquid-handling workstation for less than $400. Using this setup, we achieve reliable and flexible liquid-dispensing automation with relative pipetting errors of less than 0.3%. We show our system is well suited for several showcase applications from both the biology and chemistry fields. In support of the open-source spirit, we make all 3D models, assembly instructions, and source code ava…
Towards a fully synthetic MUC1-based anticancer vaccine: efficient conjugation of glycopeptides with mono-, di-, and tetravalent lipopeptides using c…
2011
Abstract The membrane-bound tumor-associated glycoprotein MUC1 is aberrantly glycosylated in cancer cells compared with normal cells, and is therefore considered an attractive target for cancer immunotherapy. However, tumor-associated glycopeptides from MUC1 do not elicit a sufficiently robust immune response. Therefore, antitumor vaccines were developed, which consist of MUC1 glycopeptides as the B epitopes and immune-stimulating toll-like receptor 2 (TLR 2) lipopeptide ligands. These fully synthetic vaccine candidates were prepared by solid-phase synthesis of the MUC1 glycopeptides. The Pam(3) Cys lipopeptide, also synthesized on solid-phase, was C-terminally coupled to oligovalent lysine…