Carbohydrate Research, ISSN 0008-6215, 12/2015, Volume 418, pp. 98 - 103
A new test was elaborated to identify a new set of orthogonal protecting groups. With the developed method eight different protecting groups were tested under...
Method development | Orthogonal protection | Protecting groups | PROPARGYL ETHERS | OLIGOSACCHARIDES | BIOCHEMISTRY & MOLECULAR BIOLOGY | CHEMISTRY, ORGANIC | DEPROTECTION | CHEMISTRY, APPLIED | CLEAVAGE | DERIVATIVES | Glucosides - chemistry | Biological Products - chemical synthesis | Biological Products - chemistry | Glucosides - chemical synthesis | Chromatography, High Pressure Liquid - methods | Molecular Conformation | Chemotherapy | Methods | Cancer | Analysis | Business parks | High performance liquid chromatography
Method development | Orthogonal protection | Protecting groups | PROPARGYL ETHERS | OLIGOSACCHARIDES | BIOCHEMISTRY & MOLECULAR BIOLOGY | CHEMISTRY, ORGANIC | DEPROTECTION | CHEMISTRY, APPLIED | CLEAVAGE | DERIVATIVES | Glucosides - chemistry | Biological Products - chemical synthesis | Biological Products - chemistry | Glucosides - chemical synthesis | Chromatography, High Pressure Liquid - methods | Molecular Conformation | Chemotherapy | Methods | Cancer | Analysis | Business parks | High performance liquid chromatography
Journal Article
ACS Combinatorial Science, ISSN 2156-8952, 05/2013, Volume 15, Issue 5, pp. 217 - 228
Protected peptide fragments are valuable building blocks for the assembly of large peptide sequences through fragment condensation approaches, whereas...
handles | protecting group orthogonality | solid-phase peptide synthesis | Fmoc/ t Bu strategy | protected peptides | fragment condensation approach | CHEMISTRY, MEDICINAL | 2-CHLOROTRITYL CHLORIDE RESIN | BUILDING-BLOCKS | Fmoc/tBu strategy | EFFICIENT SYNTHESIS | ACYL ISOPEPTIDE METHOD | LABILE ANCHOR GROUP | CHEMISTRY, MULTIDISCIPLINARY | SAFETY-CATCH LINKER | COMBINATORIAL CHEMISTRY | SEQUENCE-CONTAINING PEPTIDES | DIFFICULT SEQUENCE | CHEMISTRY, APPLIED | BACKBONE AMIDE LINKER | Solid-Phase Synthesis Techniques | Amino Acids - chemistry | Fluorenes - chemistry | Peptides - chemical synthesis | Synthesis | Peptides | Methodology | Fragments | Condensing | Handles | Attachment | Combinatorial analysis | Assembly
handles | protecting group orthogonality | solid-phase peptide synthesis | Fmoc/ t Bu strategy | protected peptides | fragment condensation approach | CHEMISTRY, MEDICINAL | 2-CHLOROTRITYL CHLORIDE RESIN | BUILDING-BLOCKS | Fmoc/tBu strategy | EFFICIENT SYNTHESIS | ACYL ISOPEPTIDE METHOD | LABILE ANCHOR GROUP | CHEMISTRY, MULTIDISCIPLINARY | SAFETY-CATCH LINKER | COMBINATORIAL CHEMISTRY | SEQUENCE-CONTAINING PEPTIDES | DIFFICULT SEQUENCE | CHEMISTRY, APPLIED | BACKBONE AMIDE LINKER | Solid-Phase Synthesis Techniques | Amino Acids - chemistry | Fluorenes - chemistry | Peptides - chemical synthesis | Synthesis | Peptides | Methodology | Fragments | Condensing | Handles | Attachment | Combinatorial analysis | Assembly
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 01/2014, Volume 20, Issue 5, pp. 1258 - 1262
Three structurally related relay protecting groups for carboxylic acids that are based on chelating amines have been developed. These protecting groups can...
amides | protecting groups | orthogonality | chelators | carboxylic acids | Chelators | Amides | Carboxylic acids | Orthogonality | Protecting groups | CHEMISTRY, MULTIDISCIPLINARY | Organic acids | Fluorides | Acids
amides | protecting groups | orthogonality | chelators | carboxylic acids | Chelators | Amides | Carboxylic acids | Orthogonality | Protecting groups | CHEMISTRY, MULTIDISCIPLINARY | Organic acids | Fluorides | Acids
Journal Article
Tetrahedron, ISSN 0040-4020, 2005, Volume 61, Issue 9, pp. 2493 - 2503
New deprotection conditions that provide a complete orthogonality between Tsc and Fmoc amino-protecting groups are described. The potential of these orthogonal...
Orthogonal deprotection | Branched peptide | Fmoc | Tsc | Amino-protecting group | METHYLATION | ACID | SOLID-PHASE SYNTHESIS | ANALOGS | CHEMISTRY, ORGANIC | orthogonal deprotection | THIOESTERS | amino-protecting group | AQUEOUS-SOLUTION | REMOVAL | PEPTIDE-SYNTHESIS | branched peptide | POLYAMIDES | CYCLIZATION | Peptides
Orthogonal deprotection | Branched peptide | Fmoc | Tsc | Amino-protecting group | METHYLATION | ACID | SOLID-PHASE SYNTHESIS | ANALOGS | CHEMISTRY, ORGANIC | orthogonal deprotection | THIOESTERS | amino-protecting group | AQUEOUS-SOLUTION | REMOVAL | PEPTIDE-SYNTHESIS | branched peptide | POLYAMIDES | CYCLIZATION | Peptides
Journal Article
10/2009, Volume 2009, Issue 29, 10
For regioselective deprotection studies under SPOS conditions the glucosamine derivatives 4ab/4ba, 4ac/4ca and 4ad/4da – with Fmoc/PA, Fmoc/Lev or Fmoc/Alloc,...
Carbohydrates | Glucosamine | Diols, vicinal | Oligosaccharides | Solid‐phase synthesis | Protecting groups | Solid-phase synthesis | COMPLEX | STRATEGY | CHEMISTRY, ORGANIC | HEXASACCHARIDE | LIBRARIES | SUPPORT | GLYCOSIDE-BOND FORMATION
Carbohydrates | Glucosamine | Diols, vicinal | Oligosaccharides | Solid‐phase synthesis | Protecting groups | Solid-phase synthesis | COMPLEX | STRATEGY | CHEMISTRY, ORGANIC | HEXASACCHARIDE | LIBRARIES | SUPPORT | GLYCOSIDE-BOND FORMATION
Book Review
Tetrahedron Letters, ISSN 0040-4039, 08/2015, Volume 56, Issue 35, pp. 5010 - 5012
A monosaccharide unit was synthesized bearing four different temporary protecting groups. The protecting groups used (Fmoc carbonate, NAP ether, levulinoyl and...
Monosaccharide Scaffold | Orthogonal protection | Protecting groups | Full orthogonality | LIBRARIES | DESIGN | BIOLOGICAL EVALUATION | CHEMISTRY, ORGANIC | OLIGOSACCHARIDE | Fructose
Monosaccharide Scaffold | Orthogonal protection | Protecting groups | Full orthogonality | LIBRARIES | DESIGN | BIOLOGICAL EVALUATION | CHEMISTRY, ORGANIC | OLIGOSACCHARIDE | Fructose
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 10/2015, Volume 54, Issue 42, pp. 12384 - 12388
The ability to selectively guide consecutive chemical processes towards a preferred pathway by using light of different frequencies is an appealing concept....
olefin metathesis | chromatic orthogonality | heterocycles | photochemistry | cyclization | GENERATOR | N-HETEROCYCLIC CARBENE | ISOMERIZATION | CHEMISTRY, MULTIDISCIPLINARY | ETHERS | CHEMISTRY | CYCLOISOMERIZATION | PHOTOLABILE PROTECTING GROUPS | PHOTOCHEMICAL-REACTIONS | RUTHENIUM-CARBENE CATALYST | Alkenes - chemistry | Cycloparaffins - chemistry | Stereoisomerism | Light | Cycloparaffins - chemical synthesis | Molecular Structure | Catalysis | Photochemical Processes | Sulfur compounds | Synthesis | Wavelengths | Pathways | Catalysts | Decomposition reactions | Metathesis | Activation | Orthogonality
olefin metathesis | chromatic orthogonality | heterocycles | photochemistry | cyclization | GENERATOR | N-HETEROCYCLIC CARBENE | ISOMERIZATION | CHEMISTRY, MULTIDISCIPLINARY | ETHERS | CHEMISTRY | CYCLOISOMERIZATION | PHOTOLABILE PROTECTING GROUPS | PHOTOCHEMICAL-REACTIONS | RUTHENIUM-CARBENE CATALYST | Alkenes - chemistry | Cycloparaffins - chemistry | Stereoisomerism | Light | Cycloparaffins - chemical synthesis | Molecular Structure | Catalysis | Photochemical Processes | Sulfur compounds | Synthesis | Wavelengths | Pathways | Catalysts | Decomposition reactions | Metathesis | Activation | Orthogonality
Journal Article
Carbohydrate letters, ISSN 1073-5070, 2000, Volume 4, Issue 1, pp. 21 - 27
The 1-phenyl-3-butenyl (PBU) protecting group was alternatively introduced in position 4 or 6 by regioselective opening of methyl...
Carbohydrates | Regioselection | Protecting groups
Carbohydrates | Regioselection | Protecting groups
Journal Article
Chemical Communications, ISSN 1359-7345, 1/2013, Volume 49, Issue 17, pp. 1679 - 1695
The concept of orthogonality has been applied to many areas of chemistry, ranging from wave functions to chromatography. But it was Barany and Merrifield's...
TERPYRIDINE METAL-COMPLEXES | 1,3-DIPOLAR CYCLOADDITIONS | HYDROGEN-BONDED COMPLEXES | FREE TRIAZOLE FORMATION | ONE-POT SYNTHESIS | IN-VIVO | PROTECTING GROUPS | RAPID SYNTHESIS | CHEMISTRY, MULTIDISCIPLINARY | DYNAMIC COMBINATORIAL LIBRARIES | THIOL-ENE CLICK | Binding | Self assembly | Peptides | Nanomaterials | Strategy | Activation | Nanostructure | Orthogonality
TERPYRIDINE METAL-COMPLEXES | 1,3-DIPOLAR CYCLOADDITIONS | HYDROGEN-BONDED COMPLEXES | FREE TRIAZOLE FORMATION | ONE-POT SYNTHESIS | IN-VIVO | PROTECTING GROUPS | RAPID SYNTHESIS | CHEMISTRY, MULTIDISCIPLINARY | DYNAMIC COMBINATORIAL LIBRARIES | THIOL-ENE CLICK | Binding | Self assembly | Peptides | Nanomaterials | Strategy | Activation | Nanostructure | Orthogonality
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 01/2016, Volume 22, Issue 4, pp. 1511 - 1521
The chemoselectivity of two thiol‐based modular ligations operating under mild conditions is assessed. For this purpose, a macromolecular scaffold possessing...
block copolymer | pentafluorostyrene | chemoselectivity | para-fluoro thiol | thiol–ene | thiol-ene | BLOCK-COPOLYMERS | CLICK CHEMISTRY | PORPHYRINS | CROSS-LINKING | NETWORKS | CHEMISTRY, MULTIDISCIPLINARY | SUBSTITUTION REACTION | SEQUENTIAL MICHAEL ADDITION | para-fluorothiol | POLYMER | EFFICIENT | ENE | Nuclear magnetic resonance spectroscopy | Thiols | Magnetic resonance spectroscopy | Size exclusion chromatography | Chemistry | Purification | Light irradiation | Macromolecules | Irradiation | NMR spectroscopy | Orthogonality | Light effects | Chromatography | Transformations | Modular | Scaffolds
block copolymer | pentafluorostyrene | chemoselectivity | para-fluoro thiol | thiol–ene | thiol-ene | BLOCK-COPOLYMERS | CLICK CHEMISTRY | PORPHYRINS | CROSS-LINKING | NETWORKS | CHEMISTRY, MULTIDISCIPLINARY | SUBSTITUTION REACTION | SEQUENTIAL MICHAEL ADDITION | para-fluorothiol | POLYMER | EFFICIENT | ENE | Nuclear magnetic resonance spectroscopy | Thiols | Magnetic resonance spectroscopy | Size exclusion chromatography | Chemistry | Purification | Light irradiation | Macromolecules | Irradiation | NMR spectroscopy | Orthogonality | Light effects | Chromatography | Transformations | Modular | Scaffolds
Journal Article
Organic & Biomolecular Chemistry, ISSN 1477-0520, 01/2018, Volume 16, Issue 17, pp. 3114 - 3120
A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is...
Synthesis | Sodium | Protecting groups | Alcohol | Aldehydes | Orthogonality | Acetals | Functional groups | Alcohols
Synthesis | Sodium | Protecting groups | Alcohol | Aldehydes | Orthogonality | Acetals | Functional groups | Alcohols
Journal Article
Organic Letters, ISSN 1523-7060, 07/2007, Volume 9, Issue 14, pp. 2649 - 2651
The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled...
ORGANIC-SYNTHESIS | ETHERS | 2-NITROBENZYL COMPOUNDS | CHEMISTRY, ORGANIC | REACTION-MECHANISMS | ALDEHYDES | RELEASE | PHOTOREMOVABLE PROTECTING GROUPS | CLEAVAGE | DERIVATIVES
ORGANIC-SYNTHESIS | ETHERS | 2-NITROBENZYL COMPOUNDS | CHEMISTRY, ORGANIC | REACTION-MECHANISMS | ALDEHYDES | RELEASE | PHOTOREMOVABLE PROTECTING GROUPS | CLEAVAGE | DERIVATIVES
Journal Article
Chemistry – A European Journal, ISSN 0947-6539, 07/2015, Volume 21, Issue 31, pp. 11014 - 11016
The scope of MgI2 as a valuable tool for quantitative and mild chemoselective cleavage of protecting groups is described here. This novel synthetic approach...
protecting groups | carbamates | esters | solid‐phase synthesis | cleavage reactions | solid-phase synthesis | ALPHA-AMINO | DETRITYLATION | HYDROLYSIS | DIPEPTIDE METHYL-ESTERS | CHEMISTRY, MULTIDISCIPLINARY | MILD | ALUMINUM TRICHLORIDE | AMINO ACID | TERT-BUTYL ESTERS | BENZYLIC ESTERS | EFFICIENT | Green Chemistry Technology | Solvents | Magnesium Compounds - chemical synthesis | Esters - chemistry | Magnesium Compounds - chemistry | Amino Acids - chemistry | Iodides - chemistry | Amino Acids - chemical synthesis | Iodides - chemical synthesis | Solid-Phase Synthesis Techniques - methods | Esterification | Carbamates | Esters | Methods
protecting groups | carbamates | esters | solid‐phase synthesis | cleavage reactions | solid-phase synthesis | ALPHA-AMINO | DETRITYLATION | HYDROLYSIS | DIPEPTIDE METHYL-ESTERS | CHEMISTRY, MULTIDISCIPLINARY | MILD | ALUMINUM TRICHLORIDE | AMINO ACID | TERT-BUTYL ESTERS | BENZYLIC ESTERS | EFFICIENT | Green Chemistry Technology | Solvents | Magnesium Compounds - chemical synthesis | Esters - chemistry | Magnesium Compounds - chemistry | Amino Acids - chemistry | Iodides - chemistry | Amino Acids - chemical synthesis | Iodides - chemical synthesis | Solid-Phase Synthesis Techniques - methods | Esterification | Carbamates | Esters | Methods
Journal Article
ACS Catalysis, ISSN 2155-5435, 10/2017, Volume 7, Issue 10, pp. 6821 - 6826
A highly efficient, catalytic strategy for the deprotection of classical phenacyl (Pac) as well as desyl (Dsy) protection groups has been developed using...
Photoredox catalysis | Peptide synthesis | Acids | Orthogonality | Photocleavable linker | Protecting groups | ORGANIC-SYNTHESIS | P-HYDROXYPHENACYL | CHEMISTRY, PHYSICAL | RELEASE | orthogonality | protecting groups | acids | ROBUSTNESS SCREEN | ESTERS | SYNTHETIC APPLICATIONS | RAPID ASSESSMENT | photocleavable linker | photoredox catalysis | peptide synthesis | ECONOMY | CARBOXYLIC-ACIDS
Photoredox catalysis | Peptide synthesis | Acids | Orthogonality | Photocleavable linker | Protecting groups | ORGANIC-SYNTHESIS | P-HYDROXYPHENACYL | CHEMISTRY, PHYSICAL | RELEASE | orthogonality | protecting groups | acids | ROBUSTNESS SCREEN | ESTERS | SYNTHETIC APPLICATIONS | RAPID ASSESSMENT | photocleavable linker | photoredox catalysis | peptide synthesis | ECONOMY | CARBOXYLIC-ACIDS
Journal Article
Synlett, ISSN 0936-5214, 11/2004, Volume 2004, Issue 13, pp. 2268 - 2274
ABSTRACT A major challenge in organic synthesis is the selective reaction of a functional group in the presence of others. This can be achieved by using an...
account | Cleavage | Chromophores | Protecting groups | Photochemistry | chromophores | protecting groups | cleavage | photochemistry | SOLID-PHASE SYNTHESIS | CHEMISTRY, ORGANIC | PHOTOLYSIS | LINKER | AMIDES
account | Cleavage | Chromophores | Protecting groups | Photochemistry | chromophores | protecting groups | cleavage | photochemistry | SOLID-PHASE SYNTHESIS | CHEMISTRY, ORGANIC | PHOTOLYSIS | LINKER | AMIDES
Journal Article
Pure and Applied Chemistry, ISSN 0033-4545, 02/2006, Volume 78, Issue 2, pp. 241 - 247
Journal Article
Tetrahedron, ISSN 0040-4020, 2009, Volume 65, Issue 22, pp. 4316 - 4325
Selective deprotection of aromatic ethers bearing two protecting groups on the same aromatic ring by solid-supported acids (Amberlyst-15 and PTS-Si) was...
ALCOHOLS | MILD | SELECTIVE DEPROTECTION | ALLYL ETHERS | HYDROGENOLYSIS | CHEMISTRY, ORGANIC | PROTECTING GROUPS | NEUTRAL CONDITIONS | CATALYST | EFFICIENT | BENZYL ETHERS
ALCOHOLS | MILD | SELECTIVE DEPROTECTION | ALLYL ETHERS | HYDROGENOLYSIS | CHEMISTRY, ORGANIC | PROTECTING GROUPS | NEUTRAL CONDITIONS | CATALYST | EFFICIENT | BENZYL ETHERS
Journal Article
Green Chemistry, ISSN 1463-9262, 2018, Volume 20, Issue 2, pp. 469 - 475
The present work shows that it is possible to ring-open cyclic carbonates with unprotected amino acids in water. Fine tuning of the reaction parameters made it...
GLYCINE | GREEN & SUSTAINABLE SCIENCE & TECHNOLOGY | AQUEOUS-SOLUTIONS | NON-ISOCYANATE POLYURETHANE | GLYCEROL | ASYMMETRIC ALLYLIC ALKYLATION | NMR CHEMICAL-SHIFTS | KINETICS | 2-ALLYLOXYMETHYL-2-ETHYLTRIMETHYLENE CARBONATE | POLYMERIZATION | PROTECTING GROUPS | CHEMISTRY, MULTIDISCIPLINARY | Transformation | Thiols | Purification | Alkenes | Serine | Macromolecules | Amino acids | Carboxylic acids | Glycine | Orthogonality | Alcohols | Carbamates (tradename) | Synthesis | Carbonates | Functional groups
GLYCINE | GREEN & SUSTAINABLE SCIENCE & TECHNOLOGY | AQUEOUS-SOLUTIONS | NON-ISOCYANATE POLYURETHANE | GLYCEROL | ASYMMETRIC ALLYLIC ALKYLATION | NMR CHEMICAL-SHIFTS | KINETICS | 2-ALLYLOXYMETHYL-2-ETHYLTRIMETHYLENE CARBONATE | POLYMERIZATION | PROTECTING GROUPS | CHEMISTRY, MULTIDISCIPLINARY | Transformation | Thiols | Purification | Alkenes | Serine | Macromolecules | Amino acids | Carboxylic acids | Glycine | Orthogonality | Alcohols | Carbamates (tradename) | Synthesis | Carbonates | Functional groups
Journal Article
Green Chemistry, ISSN 1463-9262, 2018, Volume 20, Issue 2, pp. 469 - 475
The present work shows that it is possible to ring-open cyclic carbonates with unprotected amino acids in water. Fine tuning of the reaction parameters made it...
Naturvetenskap | Natural Sciences | Organisk kemi | Kemi | Chemical Sciences | Organic Chemistry
Naturvetenskap | Natural Sciences | Organisk kemi | Kemi | Chemical Sciences | Organic Chemistry
Journal Article
Pure and Applied Chemistry, ISSN 0033-4545, 01/2006, Volume 78, Issue 2, pp. 241 - 247
The photochemical liberation of functional groups is an attractive alternative to the traditional chemical approach. Several photolabile protecting groups have...
photochemistry | protecting groups | chromatic orthogonality | ORGANIC-SYNTHESIS | ORTHOGONAL PHOTOLYSIS | ALDEHYDES | CHEMISTRY, MULTIDISCIPLINARY
photochemistry | protecting groups | chromatic orthogonality | ORGANIC-SYNTHESIS | ORTHOGONAL PHOTOLYSIS | ALDEHYDES | CHEMISTRY, MULTIDISCIPLINARY
Journal Article
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