Rhamnose-Containing Compounds: Biosynthesis and Applications.
deoxythymidinediphosphate-L-rhamnose
guanosine diphosphate rhamnose
rhamnose
rhamnose biosynthesis
rhamnosyltransferase
uridine diphosphate-rhamnose
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
20 Aug 2022
20 Aug 2022
Historique:
received:
09
07
2022
revised:
12
08
2022
accepted:
15
08
2022
entrez:
26
8
2022
pubmed:
27
8
2022
medline:
30
8
2022
Statut:
epublish
Résumé
Rhamnose-associated molecules are attracting attention because they are present in bacteria but not mammals, making them potentially useful as antibacterial agents. Additionally, they are also valuable for tumor immunotherapy. Thus, studies on the functions and biosynthetic pathways of rhamnose-containing compounds are in progress. In this paper, studies on the biosynthetic pathways of three rhamnose donors, i.e., deoxythymidinediphosphate-L-rhamnose (dTDP-Rha), uridine diphosphate-rhamnose (UDP-Rha), and guanosine diphosphate rhamnose (GDP-Rha), are firstly reviewed, together with the functions and crystal structures of those associated enzymes. Among them, dTDP-Rha is the most common rhamnose donor, and four enzymes, including glucose-1-phosphate thymidylyltransferase RmlA, dTDP-Glc-4,6-dehydratase RmlB, dTDP-4-keto-6-deoxy-Glc-3,5-epimerase RmlC, and dTDP-4-keto-Rha reductase RmlD, are involved in its biosynthesis. Secondly, several known rhamnosyltransferases from
Identifiants
pubmed: 36014553
pii: molecules27165315
doi: 10.3390/molecules27165315
pmc: PMC9415975
pii:
doi:
Substances chimiques
Thymine Nucleotides
0
Uridine Diphosphate
58-98-0
Racemases and Epimerases
EC 5.1.-
Rhamnose
QN34XC755A
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : the Natural Science Foundation of Henan Province
ID : 212300410203, 202300410279
Organisme : the Key Science and Technology Innovation Demonstration Projects of Henan Province
ID : 191110110600
Organisme : the Scientific and Technological Research Project Foundation of Henan Provincial Sci-entific and Technological Department
ID : 202102310479, 222102110180
Références
J Biol Chem. 2003 Jun 13;278(24):21559-65
pubmed: 12679342
PLoS One. 2016 Feb 03;11(2):e0147907
pubmed: 26840407
J Bacteriol. 2012 Dec;194(23):6479-89
pubmed: 23002227
Microbiology (Reading). 2008 Dec;154(Pt 12):3724-3730
pubmed: 19047740
Appl Microbiol Biotechnol. 2013 Mar;97(5):1909-21
pubmed: 23053103
J Biosci Bioeng. 2012 Mar;113(3):271-8
pubmed: 22100898
ACS Chem Biol. 2013 Feb 15;8(2):387-96
pubmed: 23138692
Chem Commun (Camb). 2020 Nov 21;56(90):13959-13962
pubmed: 33079080
Org Biomol Chem. 2008 Feb 7;6(3):477-84
pubmed: 18219417
J Bacteriol. 2002 Jun;184(12):3392-5
pubmed: 12029057
Clin Microbiol Rev. 2015 Jul;28(3):871-99
pubmed: 26085553
Appl Microbiol Biotechnol. 2019 Oct;103(19):7997-8008
pubmed: 31414160
J Biol Chem. 2001 Feb 23;276(8):5577-83
pubmed: 11096116
J Bacteriol. 2008 Mar;190(6):1857-65
pubmed: 18178733
Anticancer Agents Med Chem. 2008 Jan;8(1):86-91
pubmed: 18220508
Org Lett. 2007 Mar 1;9(5):857-60
pubmed: 17286408
Chembiochem. 2008 Oct 13;9(15):2506-14
pubmed: 18798210
Chemistry. 2022 Mar 16;28(16):e202200146
pubmed: 35106843
Structure. 2000 Feb 15;8(2):123-35
pubmed: 10673432
Enzyme Microb Technol. 2022 Aug;158:110040
pubmed: 35462273
Bioconjug Chem. 2016 Apr 20;27(4):1112-8
pubmed: 26978574
Mol Microbiol. 2001 May;40(3):708-18
pubmed: 11359576
Structure. 2002 Jun;10(6):773-86
pubmed: 12057193
J Biol Chem. 1980 Oct 25;255(20):9900-6
pubmed: 6159350
Org Lett. 2003 Mar 20;5(6):933-6
pubmed: 12633109
Int J Biol Macromol. 2021 Dec 15;193(Pt B):1294-1300
pubmed: 34757131
Bioorg Med Chem. 2021 Nov 15;50:116477
pubmed: 34757294
Mol Microbiol. 2013 Sep;89(5):918-28
pubmed: 23826905
Asian Pac J Trop Med. 2011 Apr;4(4):266-70
pubmed: 21771467
Nat Plants. 2018 Sep;4(9):669-676
pubmed: 30082766
J Biol Chem. 2002 Nov 15;277(46):44214-9
pubmed: 12171937
Acta Crystallogr D Biol Crystallogr. 2000 Nov;56(Pt 11):1501-4
pubmed: 11053865
Biochem Soc Trans. 2016 Feb;44(1):129-42
pubmed: 26862198
FEBS Lett. 1999 Aug 13;456(3):370-4
pubmed: 10462046
ACS Chem Biol. 2011 Feb 18;6(2):185-91
pubmed: 21043478
Biochemistry. 2002 Dec 31;41(52):15578-89
pubmed: 12501186
Front Cell Infect Microbiol. 2020 Apr 28;10:185
pubmed: 32411621
Chembiochem. 2011 Nov 4;12(16):2418-20
pubmed: 21953983
J Bacteriol. 2008 May;190(9):3147-54
pubmed: 18326581
Bioconjug Chem. 2013 Mar 20;24(3):363-75
pubmed: 23444835
Org Lett. 2008 Jan 17;10(2):161-3
pubmed: 18092787
J Biol Chem. 2012 Jan 6;287(2):879-92
pubmed: 22102281
Biochim Biophys Acta. 2015 Oct;1854(10 Pt A):1476-86
pubmed: 26116145
J Bacteriol. 2007 Nov;189(21):7856-76
pubmed: 17766420
Acta Medica (Hradec Kralove). 2008;51(2):113-9
pubmed: 18998363
J Biol Chem. 2013 Apr 19;288(16):11093-105
pubmed: 23436655
Microbiol Mol Biol Rev. 1999 Sep;63(3):523-53
pubmed: 10477307
Plant J. 2019 Jul;99(2):257-269
pubmed: 30893500
J Biol Chem. 1960 Aug;235:2196-201
pubmed: 13850250
J Bacteriol. 2001 Oct;183(19):5632-8
pubmed: 11544225
Biochem Biophys Res Commun. 2002 Jul 12;295(2):230-5
pubmed: 12150936
Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13397-402
pubmed: 12374866
Microbiology (Reading). 2003 Aug;149(Pt 8):2005-2013
pubmed: 12904540
J Biol Chem. 2007 Jun 8;282(23):16942-7
pubmed: 17434871
J Drug Target. 2010 Dec;18(10):794-802
pubmed: 21047273
Nat Chem Biol. 2015 Apr;11(4):266-70
pubmed: 25686373
J Am Chem Soc. 2010 Dec 8;132(48):17236-46
pubmed: 21080675
Bioorg Med Chem. 2010 Jan 15;18(2):896-908
pubmed: 19969466
PLoS One. 2013 Dec 31;8(12):e83810
pubmed: 24391831
Structure. 2003 Jun;11(6):715-23
pubmed: 12791259
Mol Microbiol. 1998 Jun;28(6):1103-19
pubmed: 9680202
Biotechnol Bioeng. 2003 Nov 20;84(4):452-8
pubmed: 14574703
Org Biomol Chem. 2009 Nov 7;7(21):4428-36
pubmed: 19830291
ACS Chem Biol. 2016 May 20;11(5):1205-9
pubmed: 26982552
Chem Sci. 2021 May 4;12(21):7533-7546
pubmed: 34163844
Expert Rev Vaccines. 2004 Dec;3(6):655-63
pubmed: 15606349
Chem Commun (Camb). 2016 Nov 29;52(97):13995-13998
pubmed: 27849064
J Mol Biol. 2007 Jan 5;365(1):146-59
pubmed: 17046787
Proc Natl Acad Sci U S A. 2013 Aug 20;110(34):13956-60
pubmed: 23918378
J Bacteriol. 2013 Dec;195(24):5469-78
pubmed: 24097952
J Biol Chem. 2019 Oct 18;294(42):15237-15256
pubmed: 31506299
Chem Commun (Camb). 2009 Jan 8;(2):238-40
pubmed: 19099081
J Biol Chem. 2011 Apr 15;286(15):13235-43
pubmed: 21317292
Int J Biol Macromol. 2022 Jan 1;194:706-714
pubmed: 34813790
Biochim Biophys Acta. 1961 Jul 22;51:169-71
pubmed: 13705933
J Biol Chem. 1965 Jan;240:398-405
pubmed: 14253442
Org Biomol Chem. 2019 Jan 31;17(5):1071-1075
pubmed: 30648163
Carbohydr Polym. 2022 Feb 1;277:118839
pubmed: 34893256
Microbiology (Reading). 2003 Sep;149(Pt 9):2463-2474
pubmed: 12949172
Biochem Biophys Res Commun. 2006 Jan 6;339(1):191-5
pubmed: 16297878
Biochemistry. 2015 Mar 3;54(8):1703-7
pubmed: 25647009
Biomacromolecules. 2020 Feb 10;21(2):793-802
pubmed: 31829561
FEBS J. 2009 May;276(10):2686-2700
pubmed: 19459932
Bioconjug Chem. 2016 Jan 20;27(1):110-20
pubmed: 26595674
J Bacteriol. 1996 Nov;178(22):6459-65
pubmed: 8932301
J Org Chem. 2021 Jul 2;86(13):8683-8694
pubmed: 34138579
J Bacteriol. 2010 Nov;192(21):5700-8
pubmed: 20817766
J Proteome Res. 2009 Sep;8(9):4301-10
pubmed: 19624168
Angew Chem Int Ed Engl. 2001 Apr 17;40(8):1502-1505
pubmed: 29712364
Nat Struct Biol. 2000 May;7(5):398-402
pubmed: 10802738
Planta Med. 2013 May;79(8):639-45
pubmed: 23576176
Angew Chem Int Ed Engl. 2008;47(51):9814-59
pubmed: 19058170
J Bacteriol. 2019 Jun 10;201(13):
pubmed: 31010899
Acta Crystallogr D Biol Crystallogr. 1999 Mar;55(Pt 3):706-8
pubmed: 10089454
J Biol Chem. 2007 Feb 23;282(8):5389-403
pubmed: 17190829
Acta Crystallogr D Biol Crystallogr. 2004 May;60(Pt 5):895-902
pubmed: 15103135
Curr Opin Chem Biol. 2008 Oct;12(5):556-64
pubmed: 18678278
Clin Microbiol Infect. 2012 Oct;18 Suppl 5:15-24
pubmed: 22882735
J Org Chem. 2013 Oct 4;78(19):9822-33
pubmed: 24020932
J Biol Chem. 2008 Jul 25;283(30):21120-33
pubmed: 18515358
Microbiology (Reading). 2012 Apr;158(Pt 4):908-916
pubmed: 22262098
J Mol Biol. 2010 Mar 26;397(2):436-47
pubmed: 20097205
Carbohydr Polym. 2020 Apr 1;233:115857
pubmed: 32059908
Curr Opin Chem Biol. 2009 Dec;13(5-6):608-17
pubmed: 19766052
Chembiochem. 2003 May 9;4(5):443-6
pubmed: 12740816
Nat Struct Biol. 2001 Jun;8(6):545-51
pubmed: 11373625
J Biol Chem. 1963 Oct;238:3155-60
pubmed: 14085355
Mol Plant Microbe Interact. 2011 Dec;24(12):1513-21
pubmed: 22066901
Biochem J. 2021 Feb 26;478(4):685-701
pubmed: 33599745
J Biol Chem. 2009 Mar 13;284(11):7352-63
pubmed: 19126547
Org Biomol Chem. 2018 Jan 17;16(3):452-458
pubmed: 29265155
Molecules. 2020 Jul 09;25(14):
pubmed: 32659971
J Biol Chem. 2004 Oct 15;279(42):43540-6
pubmed: 15294902
Front Microbiol. 2021 Nov 08;12:772839
pubmed: 34819927
J Sep Sci. 2011 Oct;34(19):2559-65
pubmed: 21812112
Bioorg Med Chem. 2004 Apr 1;12(7):1577-84
pubmed: 15112655
Int J Biol Macromol. 2021 Jan 1;166:1230-1237
pubmed: 33159946
Cancer Res. 1985 Jun;45(6):2405-14
pubmed: 3886132
Chembiochem. 2004 Jan 3;5(1):16-25
pubmed: 14695508
Structure. 2002 Jan;10(1):81-92
pubmed: 11796113
Mar Drugs. 2021 Sep 17;19(9):
pubmed: 34564184
Bioorg Med Chem Lett. 2012 May 1;22(9):3244-7
pubmed: 22464132
ACS Chem Biol. 2012 Jan 20;7(1):235-40
pubmed: 22013921
ACS Chem Biol. 2018 Aug 17;13(8):2130-2142
pubmed: 29916701
Biochemistry. 2012 Feb 14;51(6):1213-22
pubmed: 22283226
Glycoconj J. 2022 Jun;39(3):393-411
pubmed: 35166992
J Med Chem. 2022 Jan 13;65(1):323-332
pubmed: 34962121
J Bacteriol. 2010 Oct;192(19):5053-62
pubmed: 20675481
Biochemistry. 2008 Aug 19;47(33):8719-25
pubmed: 18656961
Medchemcomm. 2011 Jan 1;2(6):524-530
pubmed: 21927709
J Biol Chem. 1994 Aug 5;269(31):19787-95
pubmed: 8051059
Protein Sci. 2004 Feb;13(2):529-39
pubmed: 14739333
Appl Microbiol Biotechnol. 2009 Feb;82(1):13-23
pubmed: 19082588
J Am Chem Soc. 2013 Oct 2;135(39):14462-72
pubmed: 23944352
J Biol Chem. 1999 Aug 27;274(35):25069-77
pubmed: 10455186
Oncol Lett. 2018 Oct;16(4):5172-5178
pubmed: 30250584
Adv Exp Med Biol. 2001;491:369-402
pubmed: 14533809