Synthesis of Porphyrin and Bacteriochlorin Glycoconjugates through CuAAC Reaction Tuning

被引：22

作者：

Bennion, Matthew C. ^{[1
]}

Burch, Morgan A. ^{[2
]}

Dennis, David G. ^{[1
]}

Lech, Melissa E. ^{[1
]}

Neuhaus, Kira ^{[2
,3
]}

Fendler, Nikole L. ^{[2
]}

Parris, Matthew R. ^{[1
]}

Cuadra, Jessica E. ^{[1
]}

Dixon, Charlie F. ^{[1
]}

Mukosera, George T. ^{[2
]}

Blauch, David N. ^{[2
]}

Hartmann, Laura ^{[3
]}

Snyder, Nicole L. ^{[2
]}

Ruppel, Joshua, V ^{[1
]}

机构：

[1] Univ South Carolina Upstate, Div Nat Sci & Engn, 800 Univ Way, Spartanburg, SC 29303 USA

[2] Davidson Coll, Dept Chem, 102 North Main St, Davidson, NC 28035 USA

[3] Heinrich Heine Univ Dusseldorf, Inst Organ Chem & Macromol Chem, Univ Str 1, D-40225 Dusseldorf, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 38期

基金：

美国国家科学基金会;

关键词：

Bacteriochlorin; Click chemistry; Cycloaddition; Glycoconjugates; Porphyrinoids; 1,3-DIPOLAR CYCLOADDITION; CLICK-CHEMISTRY; GLYCOPORPHYRIN DERIVATIVES; PHOTODYNAMIC THERAPY; D-GALACTOSE; GLYCOCLUSTERS; EPOXIDATION; CHLORINS; SUGAR; ACID;

D O I：

10.1002/ejoc.201901128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rapid and reproducible access to a series of unique porphyrin and bacteriochlorin glycoconjugates, including meso-glycosylated porphyrins and bacteriochlorins, and beta-glycosylated porphyrins, using copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) is reported for the first time. The work presented highlights the system-dependent reaction conditions required for CuAAC glycosylation to porphyrins and bacteriochlorins based on the unique electronic properties of each ring system. Optimized reaction conditions were used to synthesize fifteen new glycosylated porphyrin and bacteriochlorin analogs in 74-99 % yield, and were extended to solid support to produce the first oligo(amidoamine)-based porphyrin glycoconjugate. These compounds hold significant potential as next-generation water-soluble catalysts and photodynamic therapy/photodynamic inactivation (PDT/PDI) agents.

引用

页码：6496 / 6503

页数：8

共 50 条

[41] Reaction of Corey Ylide with α,β-Unsaturated Ketones: Tuning of Chemoselectivity toward Dihydrofuran Synthesis
Chagarovsky, Alexey O.
Budynina, Ekaterina M.
Ivanova, Olga A.
Villemson, Elena V.
Rybakov, Victor B.
Trushkov, Igor V.
Melnikov, Mikhail Ya.
ORGANIC LETTERS, 2014, 16 (11) : 2830 - 2833
[42] Synthesis of well-defined glycopolymers with highly ordered sugar units in the side chain via combining CuAAC reaction and ROMP: lectin interaction study in homo- and hetero-glycopolymers
Liu, Zhifeng
Zhu, Yu
Ye, Wenling
Wu, Tong
Miao, Dengyun
Deng, Wei
Liu, Meina
POLYMER CHEMISTRY, 2019, 10 (29) : 4006 - 4016
[43] Facile synthesis of tetrahydroquinolines and julolidines through multicomponent reaction
Legros, Julien
Crousse, Benoit
Ourevitch, Michele
Bonnet-Delpon, Daniele
SYNLETT, 2006, (12) : 1899 - 1902
[44] Synthesis of 2-Aminopyridine Derivatives via a Tandem CuAAC/Ring-Cleavage/[4+2]-Cycloaddition/Rearrangement Reaction Sequence
Yang, Weiguang
Li, Guanrong
Luo, Danyang
Huang, Zixin
Banwell, Martin G.
Luo, Xiai
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (17) : 3689 - 3694
[45] Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2+3]cycloaddition reaction in aqueous medium
El-Remaily, Mahmoud Abd El Aleem Ali Ali
Elhady, O. M.
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (08)
[46] Synthesis of functionalized pyrroles and fused pyrroles through intermolecular [3+2] cycloaddition reaction
Prasad, Pulaganti Vijaya
Shanker, Medi
Venkanna, Avudoddi
Swamy, Marapala Kumara
Gopichand, K.
Rao, Pallapothula Venkateswar
SYNTHETIC COMMUNICATIONS, 2018, 48 (09) : 1040 - 1044
[47] 'In situ' generated 'HCI' - An efficient catalyst for solvent-free Hantzsch reaction at room temperature: Synthesis of new dihydropyridine glycoconjugates
Sharma, GVM
Reddy, KL
Lakshmi, PS
Krishna, PR
SYNTHESIS-STUTTGART, 2006, (01): : 55 - 58
[48] Synthesis of 20-O-linked 20(S)-camptothecin glycoconjugates:: Impact of the side chain of the ester-linked amino acid on epimerization during the acylation reaction and on hydrolytic stability of the final glycoconjugates
Lerchen, HG
von dem Bruch, K
JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY, 2000, 342 (08): : 753 - 760
[49] Synthesis of Molecular Tweezers Derived from Chenodeoxycholic Acid through Click Reaction and Their Recogniton Properties
Zhao, Zhigang
Wang, Xiaohong
Shi, Zhichuan
Cheng, Yuyu
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (06) : 1110 - 1117
[50] Synthesis of water soluble PEGylated (copper) phthalocyanines via Mitsunobu reaction and Cu(I)-catalysed azide-alkyne cycloaddition (CuAAC) "click" chemistry
Li, Muxiu
Khoshdel, Ezat
Haddleton, David M.
POLYMER CHEMISTRY, 2013, 4 (16) : 4405 - 4411

← 1 2 3 4 5 →