Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition
العنوان: | Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition |
---|---|
المؤلفون: | Jeffrey W. Schubert, Olivia Zhang |
المصدر: | The Journal of Organic Chemistry. 85:6225-6232 |
بيانات النشر: | American Chemical Society (ACS), 2020. |
سنة النشر: | 2020 |
مصطلحات موضوعية: | chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Organic Chemistry, Structural diversity, Tripeptide, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Amino acid, chemistry.chemical_compound, Dehydroalanine, Amines, Amino Acids, Peptides, Derivatization, Oxidation-Reduction, Conjugate |
الوصف: | Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the development of novel methods to increase the structural diversity of the unnatural amino acid pool is needed. Herein, a photoredox-mediated decarboxylative radical conjugate addition to dehydroalanine derivatives is disclosed. Mild, robust, and general conditions were identified and applied to the diastereoselective synthesis of unnatural amino acids and the late-stage derivatization of a tripeptide. |
تدمد: | 1520-6904 0022-3263 |
DOI: | 10.1021/acs.joc.0c00635 |
URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9bbebae948e761e2c1332b082fd66d71 https://doi.org/10.1021/acs.joc.0c00635 |
Rights: | CLOSED |
رقم الانضمام: | edsair.doi.dedup.....9bbebae948e761e2c1332b082fd66d71 |
قاعدة البيانات: | OpenAIRE |
ResultId |
1 |
---|---|
Header |
edsair OpenAIRE edsair.doi.dedup.....9bbebae948e761e2c1332b082fd66d71 870 3 unknown 869.657287597656 |
PLink |
https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&scope=site&db=edsair&AN=edsair.doi.dedup.....9bbebae948e761e2c1332b082fd66d71&custid=s6537998&authtype=sso |
FullText |
Array
(
[Availability] => 0
)
Array ( [0] => Array ( [Url] => https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9bbebae948e761e2c1332b082fd66d71# [Name] => EDS - OpenAIRE [Category] => fullText [Text] => View record in OpenAIRE [MouseOverText] => View record in OpenAIRE ) ) |
Items |
Array
(
[Name] => Title
[Label] => Title
[Group] => Ti
[Data] => Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition
)
Array ( [Name] => Author [Label] => Authors [Group] => Au [Data] => <searchLink fieldCode="AR" term="%22Jeffrey+W%2E+Schubert%22">Jeffrey W. Schubert</searchLink><br /><searchLink fieldCode="AR" term="%22Olivia+Zhang%22">Olivia Zhang</searchLink> ) Array ( [Name] => TitleSource [Label] => Source [Group] => Src [Data] => <i>The Journal of Organic Chemistry</i>. 85:6225-6232 ) Array ( [Name] => Publisher [Label] => Publisher Information [Group] => PubInfo [Data] => American Chemical Society (ACS), 2020. ) Array ( [Name] => DatePubCY [Label] => Publication Year [Group] => Date [Data] => 2020 ) Array ( [Name] => Subject [Label] => Subject Terms [Group] => Su [Data] => <searchLink fieldCode="DE" term="%22chemistry%2Echemical%5Fclassification%22">chemistry.chemical_classification</searchLink><br /><searchLink fieldCode="DE" term="%22010405+organic+chemistry%22">010405 organic chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Chemistry%22">Chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+Chemistry%22">Organic Chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Structural+diversity%22">Structural diversity</searchLink><br /><searchLink fieldCode="DE" term="%22Tripeptide%22">Tripeptide</searchLink><br /><searchLink fieldCode="DE" term="%22010402+general+chemistry%22">010402 general chemistry</searchLink><br /><searchLink fieldCode="DE" term="%2201+natural+sciences%22">01 natural sciences</searchLink><br /><searchLink fieldCode="DE" term="%22Combinatorial+chemistry%22">Combinatorial chemistry</searchLink><br /><searchLink fieldCode="DE" term="%220104+chemical+sciences%22">0104 chemical sciences</searchLink><br /><searchLink fieldCode="DE" term="%22Amino+acid%22">Amino acid</searchLink><br /><searchLink fieldCode="DE" term="%22chemistry%2Echemical%5Fcompound%22">chemistry.chemical_compound</searchLink><br /><searchLink fieldCode="DE" term="%22Dehydroalanine%22">Dehydroalanine</searchLink><br /><searchLink fieldCode="DE" term="%22Amines%22">Amines</searchLink><br /><searchLink fieldCode="DE" term="%22Amino+Acids%22">Amino Acids</searchLink><br /><searchLink fieldCode="DE" term="%22Peptides%22">Peptides</searchLink><br /><searchLink fieldCode="DE" term="%22Derivatization%22">Derivatization</searchLink><br /><searchLink fieldCode="DE" term="%22Oxidation-Reduction%22">Oxidation-Reduction</searchLink><br /><searchLink fieldCode="DE" term="%22Conjugate%22">Conjugate</searchLink> ) Array ( [Name] => Abstract [Label] => Description [Group] => Ab [Data] => Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the development of novel methods to increase the structural diversity of the unnatural amino acid pool is needed. Herein, a photoredox-mediated decarboxylative radical conjugate addition to dehydroalanine derivatives is disclosed. Mild, robust, and general conditions were identified and applied to the diastereoselective synthesis of unnatural amino acids and the late-stage derivatization of a tripeptide. ) Array ( [Name] => ISSN [Label] => ISSN [Group] => ISSN [Data] => 1520-6904<br />0022-3263 ) Array ( [Name] => DOI [Label] => DOI [Group] => ID [Data] => 10.1021/acs.joc.0c00635 ) Array ( [Name] => URL [Label] => Access URL [Group] => URL [Data] => <link linkTarget="URL" linkTerm="https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9bbebae948e761e2c1332b082fd66d71" linkWindow="_blank">https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9bbebae948e761e2c1332b082fd66d71</link><br /><link linkTarget="URL" linkTerm="https://doi.org/10.1021/acs.joc.0c00635" linkWindow="_blank">https://doi.org/10.1021/acs.joc.0c00635</link> ) Array ( [Name] => Copyright [Label] => Rights [Group] => Cpyrght [Data] => CLOSED ) Array ( [Name] => AN [Label] => Accession Number [Group] => ID [Data] => edsair.doi.dedup.....9bbebae948e761e2c1332b082fd66d71 ) |
RecordInfo |
Array
(
[BibEntity] => Array
(
[Identifiers] => Array
(
[0] => Array
(
[Type] => doi
[Value] => 10.1021/acs.joc.0c00635
)
)
[Languages] => Array
(
[0] => Array
(
[Text] => Undetermined
)
)
[PhysicalDescription] => Array
(
[Pagination] => Array
(
[PageCount] => 8
[StartPage] => 6225
)
)
[Subjects] => Array
(
[0] => Array
(
[SubjectFull] => chemistry.chemical_classification
[Type] => general
)
[1] => Array
(
[SubjectFull] => 010405 organic chemistry
[Type] => general
)
[2] => Array
(
[SubjectFull] => Chemistry
[Type] => general
)
[3] => Array
(
[SubjectFull] => Organic Chemistry
[Type] => general
)
[4] => Array
(
[SubjectFull] => Structural diversity
[Type] => general
)
[5] => Array
(
[SubjectFull] => Tripeptide
[Type] => general
)
[6] => Array
(
[SubjectFull] => 010402 general chemistry
[Type] => general
)
[7] => Array
(
[SubjectFull] => 01 natural sciences
[Type] => general
)
[8] => Array
(
[SubjectFull] => Combinatorial chemistry
[Type] => general
)
[9] => Array
(
[SubjectFull] => 0104 chemical sciences
[Type] => general
)
[10] => Array
(
[SubjectFull] => Amino acid
[Type] => general
)
[11] => Array
(
[SubjectFull] => chemistry.chemical_compound
[Type] => general
)
[12] => Array
(
[SubjectFull] => Dehydroalanine
[Type] => general
)
[13] => Array
(
[SubjectFull] => Amines
[Type] => general
)
[14] => Array
(
[SubjectFull] => Amino Acids
[Type] => general
)
[15] => Array
(
[SubjectFull] => Peptides
[Type] => general
)
[16] => Array
(
[SubjectFull] => Derivatization
[Type] => general
)
[17] => Array
(
[SubjectFull] => Oxidation-Reduction
[Type] => general
)
[18] => Array
(
[SubjectFull] => Conjugate
[Type] => general
)
)
[Titles] => Array
(
[0] => Array
(
[TitleFull] => Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition
[Type] => main
)
)
)
[BibRelationships] => Array
(
[HasContributorRelationships] => Array
(
[0] => Array
(
[PersonEntity] => Array
(
[Name] => Array
(
[NameFull] => Jeffrey W. Schubert
)
)
)
[1] => Array
(
[PersonEntity] => Array
(
[Name] => Array
(
[NameFull] => Olivia Zhang
)
)
)
)
[IsPartOfRelationships] => Array
(
[0] => Array
(
[BibEntity] => Array
(
[Dates] => Array
(
[0] => Array
(
[D] => 09
[M] => 04
[Type] => published
[Y] => 2020
)
)
[Identifiers] => Array
(
[0] => Array
(
[Type] => issn-print
[Value] => 15206904
)
[1] => Array
(
[Type] => issn-print
[Value] => 00223263
)
[2] => Array
(
[Type] => issn-locals
[Value] => edsair
)
)
[Numbering] => Array
(
[0] => Array
(
[Type] => volume
[Value] => 85
)
)
[Titles] => Array
(
[0] => Array
(
[TitleFull] => The Journal of Organic Chemistry
[Type] => main
)
)
)
)
)
)
)
|
IllustrationInfo |