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Review
. 2010 Mar;30(2):171-257.
doi: 10.1002/med.20155.

Carbohydrate recognition by boronolectins, small molecules, and lectins

Shan Jin  1 , Yunfeng Cheng, Suazette Reid, Minyong Li, Binghe Wang
Affiliations
Review

Carbohydrate recognition by boronolectins, small molecules, and lectins

Shan Jin et al. Med Res Rev. 2010 Mar.

Abstract

Carbohydrates are known to mediate a large number of biological and pathological events. Small and macromolecules capable of carbohydrate recognition have great potentials as research tools, diagnostics, vectors for targeted delivery of therapeutic and imaging agents, and therapeutic agents. However, this potential is far from being realized. One key issue is the difficulty in the development of "binders" capable of specific recognition of carbohydrates of biological relevance. This review discusses systematically the general approaches that are available in developing carbohydrate sensors and "binders/receptors," and their applications. The focus is on discoveries during the last 5 years.

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Figures

Figure 1
Figure 1
Structures of an enantiomeric pair of α-amidoboronic acids studied for their binding with diols
Figure 2
Figure 2
Structures of boronic acid-based fluorescent reporter compounds 5–7.
Figure 3
Figure 3
Structure of compound 8
Figure 4
Figure 4
Structures of boronic acid-based fluorescent reporters 9–13
Figure 5
Figure 5
Structures of boronic acid-based reporters 14–18
Figure 6
Figure 6
Structures of compounds 20–22 in the Singaram glucose sensing system
Figure 7
Figure 7
Structure of compound 27
Figure 8
Figure 8
Structures of boronic acid-based sensors 28–29
Figure 9
Figure 9
Structures of boronic acid-based sensors 30 and 31
Figure 10
Figure 10
Structures of boronic acid-based sensor 32, complex 33, and sensor 34
Figure 11
Figure 11
Structures of boronic acid-based sensors 35 and BPR indicator 36
Figure 12
Figure 12
Structure of boronic acid-based sensor 37
Figure 13
Figure 13
Structure frame of a peptide library 1 with 289 members
Figure 14
Figure 14
Structures of ortho-hydroxymethyl phenylboronic acid 39a and its dialkylamino (Wulff type) analogue 39b as well as methyl α-D-glucopyranoside
Figure 15
Figure 15
Structure of tetramethylrhodamine-boronic acid (40, TMR-B)
Figure 16
Figure 16
Structure of polymer 44
Figure 17
Figure 17
Structures of boronic acid-based sensors on SAMs
Figure 18
Figure 18
Structures of a tridentate β-D-fructofuranose ester 51 and a macrocyclic β-D-fructopyranose diester 52
Figure 19
Figure 19
sLex structure
Figure 20
Figure 20
Structure of neomycin B
Figure 21
Figure 21
Structure of moenomycin A
Figure 22
Figure 22
The chemical structures of BTTP and MTTP
Figure 23
Figure 23
Structures of compounds 57, 58a, and 58b
Figure 24
Figure 24
Structures of compounds 59–65
Figure 25
Figure 25
Structures of compounds 66–69
Figure 26
Figure 26
Structures of compounds 70–74
Figure 27
Figure 27
Structures of compounds 75 and 76
Figure 28
Figure 28
Structures of compounds 77–85
Figure 29
Figure 29
Structures of receptors 86 and 87
Figure 30
Figure 30
Structure of crown ether receptors 88 and 89
Figure 31
Figure 31
Structures of compounds 90, 91α and 91β
Figure 32
Figure 32
Structures of pyrrolic tripodal receptors 98–105
Figure 33
Figure 33
Structures of model sugars for binding studies
Figure 34
Figure 34
Structures of 106 and 107
Figure 35
Figure 35
Structures of compounds 108 and monosaccharides 109–111
Figure 36
Figure 36
Structures of compounds 112–116
Figure 37
Figure 37
Structure of 117
Figure 38
Figure 38
Structure of compound 118
Figure 39
Figure 39
Structure of compound 119
Figure 40
Figure 40
NOESY contacts observed for the complex between β-cellobiose and receptor 119
Figure 41
Figure 41
Structures of compounds 120 and 121
Figure 42
Figure 42
Structures of hydrogen bonding-driven foldamers 122 and 123
Figure 43
Figure 43
Calix[4]arene-based ligands as endotoxin receptors 124–126
Figure 44
Figure 44
Structure of MACP-4
Figure 45
Figure 45
Transition states of MACP-4-resorcinol complex
Figure 46
Figure 46
Complex Structure proposed for boronic-acid-appended Zinc (II) porphyrin plus G-6-P
Figure 47
Figure 47
Complexation mode proposed for the two-points binding of uronic acids to the Zn(II) complex
Figure 48
Figure 48
Structure of 130 and 131
Figure 49
Figure 49
Structures of salophene-lanthanide (europium) complexes
Figure 50
Figure 50
Complexes modes with mannosed glucose
Scheme 1
Scheme 1
Binding of phenylboronic acid with a diol
Scheme 2
Scheme 2
Overall binding of phenylboronic acid with a diol
Scheme 3
Scheme 3
Mechanism of sugar sensing by the viologen-boronic acid system
Scheme 4
Scheme 4
Carbohydrate sensing using a 3-component assay with a nitronyl nitroxide quencher
Scheme 5
Scheme 5
Synthesis of a cadmium-centered tris-boronic acid receptor 26
Scheme 6
Scheme 6
Immobilization and derivatization of boronic acids using N, N-diethanolaminomethyl polystyrene (DEAM-PS 38) for combinatorial library synthesis
Scheme 7
Scheme 7
Binding between ortho-hydroxymethyl phenylboronic acid 39c and glycoconjugates
Scheme 8
Scheme 8
A strategy for the visual detection of the terminal glycosylation state of a glycoprotein
Scheme 9
Scheme 9
Arylboronic acid (41, 42)-polymer (43) based sensors for saccharides
Scheme 10
Scheme 10
Formation of a block copolymer (45, 46 and 49) containing boronic acid and acrylamido fragments via atom transfer radical (ATRP) polymerization
Scheme 11
Scheme 11
A fluorescent glucose sensing system based on ARS/PBA/DBBTAB co-vesicles
Scheme 12
Scheme 12
Schematic illustration of the modified electrode and competitive assay
Scheme 13
Scheme 13
(a) A cooperative hydrogen-bond pattern in carbohydrate complexation with 59. (b) A cooperative and secondary hydrogen-bond pattern in carbohydrate complexation with 66
Scheme 14
Scheme 14
Synthesis of the macrobicyclic cage 95
Scheme 15
Scheme 15
β-Mannoside-selective pyrrolic tripodal receptor
Scheme 16
Scheme 16
Tricatecholic receptor for carbohydrate recognition
Scheme 17
Scheme 17
Hydrogen-bond-driven saccharide recognition
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