Total Synthesis of the Photorhabdus temperata ssp. Cinereal 3240 Zwitterionic Trisaccharide Repeating Unit
Zwitterionic carbohydrate modifications, such as phosphoethanolamine (PEtN), govern host-pathogen interactions. Whereas it is recognized that these modifications stimulate the host immune system, the purpose of PEtN modification remains largely descriptive. As an enabling step toward studying this carbohydrate modification, we report a synthesis of the P. temperata zwitterionic trisaccharide repeating unit. The 32-step synthesis was enabled by H-phosphonate chemistry to install the PEtN arm on a poorly reactive and sterically hindered C4-alcohol.
Medienart: |
E-Artikel |
---|
Erscheinungsjahr: |
2021 |
---|---|
Erschienen: |
2021 |
Enthalten in: |
Zur Gesamtaufnahme - volume:23 |
---|---|
Enthalten in: |
Organic letters - 23(2021), 15 vom: 06. Aug., Seite 5922-5926 |
Sprache: |
Englisch |
---|
Beteiligte Personen: |
Nguyen, Johny M [VerfasserIn] |
---|
Links: |
---|
Themen: |
78A2BX7AEU |
---|
Anmerkungen: |
Date Completed 23.11.2021 Date Revised 07.02.2022 published: Print-Electronic Citation Status MEDLINE |
---|
doi: |
10.1021/acs.orglett.1c02023 |
---|
funding: |
|
---|---|
Förderinstitution / Projekttitel: |
|
PPN (Katalog-ID): |
NLM32858892X |
---|
LEADER | 01000naa a22002652 4500 | ||
---|---|---|---|
001 | NLM32858892X | ||
003 | DE-627 | ||
005 | 20231225203245.0 | ||
007 | cr uuu---uuuuu | ||
008 | 231225s2021 xx |||||o 00| ||eng c | ||
024 | 7 | |a 10.1021/acs.orglett.1c02023 |2 doi | |
028 | 5 | 2 | |a pubmed24n1095.xml |
035 | |a (DE-627)NLM32858892X | ||
035 | |a (NLM)34314177 | ||
040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
041 | |a eng | ||
100 | 1 | |a Nguyen, Johny M |e verfasserin |4 aut | |
245 | 1 | 0 | |a Total Synthesis of the Photorhabdus temperata ssp. Cinereal 3240 Zwitterionic Trisaccharide Repeating Unit |
264 | 1 | |c 2021 | |
336 | |a Text |b txt |2 rdacontent | ||
337 | |a ƒaComputermedien |b c |2 rdamedia | ||
338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
500 | |a Date Completed 23.11.2021 | ||
500 | |a Date Revised 07.02.2022 | ||
500 | |a published: Print-Electronic | ||
500 | |a Citation Status MEDLINE | ||
520 | |a Zwitterionic carbohydrate modifications, such as phosphoethanolamine (PEtN), govern host-pathogen interactions. Whereas it is recognized that these modifications stimulate the host immune system, the purpose of PEtN modification remains largely descriptive. As an enabling step toward studying this carbohydrate modification, we report a synthesis of the P. temperata zwitterionic trisaccharide repeating unit. The 32-step synthesis was enabled by H-phosphonate chemistry to install the PEtN arm on a poorly reactive and sterically hindered C4-alcohol | ||
650 | 4 | |a Journal Article | |
650 | 4 | |a Research Support, N.I.H., Extramural | |
650 | 4 | |a Research Support, Non-U.S. Gov't | |
650 | 7 | |a Ethanolamines |2 NLM | |
650 | 7 | |a Trisaccharides |2 NLM | |
650 | 7 | |a phosphorylethanolamine |2 NLM | |
650 | 7 | |a 78A2BX7AEU |2 NLM | |
700 | 1 | |a Townsend, Steven D |e verfasserin |4 aut | |
773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 23(2021), 15 vom: 06. Aug., Seite 5922-5926 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
773 | 1 | 8 | |g volume:23 |g year:2021 |g number:15 |g day:06 |g month:08 |g pages:5922-5926 |
856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.orglett.1c02023 |3 Volltext |
912 | |a GBV_USEFLAG_A | ||
912 | |a GBV_NLM | ||
951 | |a AR | ||
952 | |d 23 |j 2021 |e 15 |b 06 |c 08 |h 5922-5926 |