CN106674236A - TMeQ[6] and D,L-glutamine supramolecular complex as well as preparation method and application thereof - Google Patents
TMeQ[6] and D,L-glutamine supramolecular complex as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN106674236A CN106674236A CN201610995975.1A CN201610995975A CN106674236A CN 106674236 A CN106674236 A CN 106674236A CN 201610995975 A CN201610995975 A CN 201610995975A CN 106674236 A CN106674236 A CN 106674236A
- Authority
- CN
- China
- Prior art keywords
- tmeq
- product
- glutaminate
- molecular complex
- super molecular
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/62—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Electrochemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a TMeQ[6] and D,L-glutamine supramolecular complex as well as a preparation method and application thereof. The TMeQ[6] and D,L-glutamine supramolecular complex comprises a TMeQ[6]-D-glutamine supramolecular complex synthesized by water-soluble cucurbitnuril TMeQ[6] and object D-glutamine, and further comprises a TMeQ[6]-L-glutamine supramolecular complex synthesized by the water-soluble cucurbitnuril TMeQ[6] and object L-glutamine; the molecular formula of TMeQ[6]-D-glutamine is C45H56O16N26, and the structural formula is shown in the specification; and the molecular formula of TMeQ[6]-L-glutamine is C45H56O16N26, and the structural formula is shown in the specification. The TMeQ[6] and D,L-glutamine supramolecular complex has the characteristics of being capable of identifying D,L-glutamine and being stable in self-assembled structure.
Description
Technical field
The present invention relates to a kind of super molecular complex and methods for making and using same, more particularly to a kind of TMeQ [6] and D, L-
Glutamine super molecular complex and preparation method and application.
Background technology
Melon ring (Cucurbit [n] urils, Q [n] s) as the up-and-coming youngster of host compound in supramolecular chemistry, with
The structure of the hexa-atomic melon ring (Q [6]) of 1981 first member of Nian Gua rings family is determined, and melon ring homologue, derivant, similar
The continuous release of thing, melon cyclisation is learned, and the particularly research in Supramolecular self assembly field achieves the progress for attracting people's attention.Due to
Melon ring has hydrophobic cavity, and the characteristics of polar carbonyl modification port, makes melon ring not only have host molecule function, can inclusion
The suitable organic molecule of structure, size, forms distinctive melon ring host-guest chemistry；Ligand molecular is can act also as, with metal ion
And its coordination compound or compounds of group coordination, form distinctive melon ring Coordinative Chemistry.Also find in recent years, in melon ring-metal system
Middle to be introduced into suitable organic molecule or introduce metal ion in melon ring-guest molecule system, it is special with special to be obtained
The Supramolecular self assembly entity of performance.
Aminoacid (Amino acid) is the ultimate unit for constituting protein (protein), gives protein and specifically divides
Minor structure form, makes its molecule have biochemical activity.Protein is biological bioactive molecule important in vivo, including is catalyzed new old
The enzyme of metabolism.Two or more chemistry of amino acids aggregate into peptide, and the original segments of a protein are that protein is generated
Precursor.
Aminoacid is broadly referred to not only containing a basic amine group but also containing the organic compound of an acidic carboxypolymer, as
As its name is described.But general aminoacid, then refer to the structural units for constituting protein.In biosphere, constitute
There is the aminoacid of native protein its specific construction features, i.e. its amino to be connected directly between on alpha -carbon atom.It is chiral or not
Symmetry material be containing asymmetric carbon it is former in compound, this kind of compound generally existing in chemistry and life sciences.From
So in boundary, most molecules (such as sugar, aminoacid) and the biomacromolecule (such as protein, DNA) that is made up of them are in sky
Between all there is in structure unsymmetry so that organism can highly select a certain specific chiral molecule of identification, so as to produce
Raw biological agent.
Molecular recognition may be defined as such a process, the receptor given for, the key therewith of substrate selective
Close.Thus, select and bonding is two aspects for recognizing.Specifically, molecular recognition process need to follow two principles, i.e., complementary
Property and pre-organized principle.What intermolecular weak interaction power adduction under certain condition and synergism were formed has certain orientation
Property and selective high forces, become the predominant intermolecular forces of molecular recognition and self assembly.
The content of the invention
It is an object of the invention to provide a kind of TMeQ [6] and D, L-glutaminate super molecular complex is of the present invention
TMeQ [6] and D, L-glutaminate super molecular complex have be capable of identify that D, the stable spy of L-glutaminate and self-assembled structures
Point.
What the present invention was realized in：A kind of TMeQ [6] and D, L-glutaminate super molecular complex, including water solublity melon
TMeQ [6]-D-Gln super molecular complex that ring TMeQ [6] synthesizes with object D-Gln, also including water solublity melon
TMeQ [6]-L-glutaminate super molecular complex that ring TMeQ [6] synthesizes with object L-glutaminate；Described TMeQ [6]-
The molecular formula of D-Gln is C45H56O16N26, structural formula is：
The molecular formula of described TMeQ [6]-L-glutaminate is C45H56O16N26, structural formula is：
Aforesaid TMeQ [6] and D, L-glutaminate super molecular complex is prepared according to the following steps：
A. TMeQ [6] is used into dissolving with hydrochloric acid, obtains A product；
B. A product are divided into into two parts, it is a to mix with excessive object D-Gln, B product are obtained, the visitor of another and excess
Body L-glutaminate mixes, and obtains C product；
C. B product and C product are heated respectively, is stood after heating until there is crystallization, the crystallization in B product is TMeQ [6]-D-
Glutamine super molecular complex, the crystallization in C product is TMeQ [6]-L-glutaminate super molecular complex.
More preferably, aforesaid TMeQ [6] and D, L-glutaminate super molecular complex is prepared according to the following steps：
A. TMeQ [6] is used into dissolving with hydrochloric acid, obtains A product；
B. A product are divided into two parts, a amount ratio that TMeQ [6] compounds and the material of object are pressed with object D-Gln
For 0.8~1.0:3~5 ratio mixing, obtains B product；Another presses TMeQ [6] compounds with object with object L-glutaminate
The amount ratio of material is 0.8~1.0:3~5 ratio mixing, obtains C product；Respectively by two portions of mixed liquors at 55~60 DEG C after mixing
2~3min of heating；
C. 2~3min heating is heated respectively at 55~60 DEG C to B product and C product, stands 11~14 days, until there is knot
Crystalline substance, the ratio for finally respectively obtaining two kinds of stable Subjective and Objective is 1:Crystallization in 1 super molecular complex, i.e. B product is TMeQ
[6]-D-Gln super molecular complex, the crystallization in C product is TMeQ [6]-L-glutaminate super molecular complex.
Aforesaid TMeQ [6] and D, L-glutaminate super molecular complex is used to recognize D-Gln and L- glutamy
Amine.
Beneficial effect：Compared with prior art, TMeQ [6] of the invention and D, the crystalline substance of L-glutaminate super molecular complex
There is the hydrone of a macrocyclic ligand TMeQ [6], a D, L-glutaminate molecule and a coordination in body unit.D, L- paddy ammonia
The chiral radicals of amide molecule are located at outside TMeQ [6] port, and the hydrogen atom on its alkyl and amino can be with the ketonic oxygen of TMeQ [6]
Atom forms hydrogen bond, and remaining group is entered and is coordinated therewith in the cavity of melon ring, and terminal amino group is by hydrone and the carbonyl of TMeQ [6]
Base oxygen atom ligand；By the structure so as to which self-assembled structures are more stable.It is illustrated in figure 3 TMeQ [6] and D- glutamy
The supermolecule chain structure of amine complex.Hydrogen atom on the carboxyl and glycosides urea unit of D-Gln, methyl is right with another
All there is hydrogen bond action in the carbonylic oxygen atom for claiming Tetramethyl melon ring, and constituted oversubscription by the interaction between them
Sub- chain structure.
The Symmetric tetramethyl cucurbituril (TMeQ [6]) and D of the present invention, L-glutaminate molecule Supramolecular self assembly leads to
Cross and the structural information of biomolecule is converted to into physiochemical signal, and Symmetric tetramethyl cucurbituril has hydrophobic cavity,
Have suitable cavity size, can inclusion aminoacid form Supramolecular self assembly body, and D-Gln, L-glutaminate molecule
Chiral radicals it is still exposed outside melon ring, achirality enters partly into melon annular space chamber the inside, therefore to D-Gln, L- paddy
The molecular recognition of glutamine this opponent's acidic amino acid provides advantage, so that super with TMeQ [6] as supermolecule main block
Molecular complex can be used in optionally recognizing D-Gln, L-glutaminate, to make the life with specific selectivity
Thing material.
Present invention crystal data display TMeQ [6] (i.e. Symmetrical Tetramethyl melon as X-ray single crystal diffractometer obtained by
Cycle compound) with D-Gln, L-glutaminate formed Subjective and Objective material amount ratio be 1:1 binding mode；As a result prove
TMeQ [6] respectively with D-Gln, L-glutaminate can be formed Subjective and Objective ratio be 1:1 super molecular complex, its knot
Structure is as depicted in figs. 1 and 2.
The X-ray diffraction (as shown in Figure 4) of TMeQ [6]-D-Gln is investigated using powder diffraction methods, TMeQ [6]-
The X-ray diffraction (as shown in Figure 5) of L-glutaminate, and with the relative analyses of the X-ray diffraction spectrogram of known amorphous material
It was found that：The X-ray diffractogram of sample is with the X-ray diffraction spectrogram of amorphous material in diffraction maximum number, angle position, relative intensity
Order and diffraction maximum are all coincide in shape substantially, so as to the monocrystalline for confirming gained is pure phase.
Fig. 6 is illustrated, and using MALDI-TOF-MS D-Gln and TMeQ have been investigated
[6] situation of host-guest inclusion complex is formed.TMeQ [6] forms the mass spectrum of inclusion complexes, m/z with D-Gln
1092.06 is TMeQ [6]+K+(theoretical value 1092.04), m/z 1200.56 is TMeQ [6]+D-Gln (theoretical value
1199.14).Mass spectral results show that TMeQ [6] forms 1 with D-Gln：1 host-guest inclusion complex, its result and list
Brilliant diffractive technology analysis is consistent.
The present invention can significantly recognize D-Gln and L-glutaminate, D-Gln, L- by crystal structure
The chiral radicals of glutamine molecule are still exposed outside melon ring, and achirality enters partly into melon annular space chamber the inside so that coordinate
Thing also carries chirality, such that it is able to recognize D-Gln and L-glutaminate.
Description of the drawings
Fig. 1 is the structural formula of TMeQ [the 6]-D-Gln super molecular complex obtained by X-ray single crystal diffractometer；
Fig. 2 is the structural formula of TMeQ [the 6]-L-glutaminate super molecular complex obtained by X-ray single crystal diffractometer；
Fig. 3 is the one-dimensional supermolecule chain structure that TMeQ [6] interacts with D-Gln；
Fig. 4 is the X-ray powder diffraction pattern of TMeQ [6]-D-Gln；
Fig. 5 is the X-ray powder diffraction pattern of TMeQ [6]-L-glutaminate；
Fig. 6 schemes for the MS of TMeQ [6]-D-Gln super molecular complex.
Specific embodiment
Embodiment 1.A kind of TMeQ [6] and D, L-glutaminate super molecular complex, including water solublity melon ring TMeQ [6] with
Object D-Gln synthesis TMeQ [6]-D-Gln super molecular complex, also including water solublity melon ring TMeQ [6] with
TMeQ [the 6]-L-glutaminate super molecular complex of object L-glutaminate synthesis；Described TMeQ [6]-D-Gln
Molecular formula is C45H56O16N26, structural formula is：
The molecular formula of described TMeQ [6]-L-glutaminate is C45H56O16N26, structural formula is：
Aforesaid TMeQ [6] and D, the preparation method of L-glutaminate super molecular complex, are prepared according to the following steps：
A. TMeQ [6] is used into dissolving with hydrochloric acid, obtains A product；
B. A product are divided into into two parts, it is a to mix with excessive object D-Gln, B product are obtained, the visitor of another and excess
Body L-glutaminate mixes, and obtains C product；
C. B product and C product are heated respectively, is stood after heating until there is crystallization, the crystallization in B product is TMeQ [6]-D-
Glutamine super molecular complex, the crystallization in C product is TMeQ [6]-L-glutaminate super molecular complex.
More preferably, aforesaid TMeQ [6] and D, the preparation method of L-glutaminate super molecular complex, make in the steps below
It is standby：
A. TMeQ [6] is used into dissolving with hydrochloric acid, obtains A product；
B. A product are divided into two parts, a amount ratio that TMeQ [6] compounds and the material of object are pressed with object D-Gln
For 0.8~1.0:3~5 ratio mixing, obtains B product；Another presses TMeQ [6] compounds with object with object L-glutaminate
The amount ratio of material is 0.8~1.0:3~5 ratio mixing, obtains C product；Respectively by two portions of mixed liquors at 55~60 DEG C after mixing
2~3min of heating；
C. 2~3min heating is heated respectively at 55~60 DEG C to B product and C product, stands 11~14 days, until there is knot
Crystalline substance, the ratio for finally respectively obtaining two kinds of stable Subjective and Objective is 1:Crystallization in 1 super molecular complex, i.e. B product is TMeQ
[6]-D-Gln super molecular complex, the crystallization in C product is TMeQ [6]-L-glutaminate super molecular complex.
Aforesaid TMeQ [6] and D, L-glutaminate super molecular complex is used to recognize D-Gln and L- glutamy
Amine.
Embodiment 2.A kind of TMeQ [6] and D, L-glutaminate super molecular complex, including water solublity melon ring TMeQ [6] with
Object D-Gln synthesis TMeQ [6]-D-Gln super molecular complex, also including water solublity melon ring TMeQ [6] with
TMeQ [the 6]-L-glutaminate super molecular complex of object L-glutaminate synthesis；Described TMeQ [6]-D-Gln
Molecular formula is C45H56O16N26, structural formula is：
The molecular formula of described TMeQ [6]-L-glutaminate is C45H56O16N26, structural formula is：
Aforesaid TMeQ [6] and D, the preparation method of L-glutaminate super molecular complex, are prepared according to the following steps：
A. 30mg TMeQ [6] are completely dissolved with the hydrochloric acid of 5mL, obtain solution A；
B. solution A is divided into two parts, a amount that TMeQ [6] compounds and the material of object are pressed with object D-Gln
Than for 1:4 ratio mixing, obtains mixed liquor；Another presses the material of TMeQ [6] compounds and object with object L-glutaminate
Amount ratio be 1:4 ratio mixing, obtains mixed liquor；Respectively two portions of mixed liquors are heated into 2min at 55 DEG C after mixing；
C. after heating, 14 days are stood, until there is crystallization, the ratio for finally respectively obtaining two kinds of stable Subjective and Objective is 1:1
Super molecular complex, i.e. TMeQ [6]-D-Gln super molecular complex, the molecular formula of the super molecular complex is
C45H56O16N26；TMeQ [6]-L-glutaminate super molecular complex, the molecular formula of the super molecular complex is C45H56O16N26。
Embodiment 3.A kind of TMeQ [6] and D, L-glutaminate super molecular complex, including water solublity melon ring TMeQ [6] with
Object D-Gln synthesis TMeQ [6]-D-Gln super molecular complex, also including water solublity melon ring TMeQ [6] with
TMeQ [the 6]-L-glutaminate super molecular complex of object L-glutaminate synthesis；Described TMeQ [6]-D-Gln
Molecular formula is C45H56O16N26, structural formula is：
The molecular formula of described TMeQ [6]-L-glutaminate is C45H56O16N26, structural formula is：
Aforesaid TMeQ [6] and D, the preparation method of L-glutaminate super molecular complex, are prepared according to the following steps：
A. two parts of TMeQ [6] (20mg) are put in two beakers, with 4mL hydrochloric acid solutions heating for dissolving and shake number respectively
It is complete that minute is allowed to dissolving；
B. D-Glu (10mg) is weighed respectively, and L-glutaminate (10mg) solid is in the beaker for filling TMeQ [6]；
C. again two beakers are heated into 2min at 55~65 DEG C, into beaker without precipitating or have a small amount of precipitation, cooling
To room temperature and stand, have the clear crystal for being suitable to crystal structure determination to separate out after about 12 days, yield is 30% or so.
Claims (4)
1. a kind of TMeQ [6] and D, L-glutaminate super molecular complex, it is characterised in that：Including water solublity melon ring TMeQ [6]
TMeQ [the 6]-D-Gln super molecular complex synthesized with object D-Gln, also including water solublity melon ring TMeQ [6]
With TMeQ [the 6]-L-glutaminate super molecular complex of object L-glutaminate synthesis；Described TMeQ [6]-D-Gln
Molecular formula be C45H56O16N26, structural formula is：
The molecular formula of described TMeQ [6]-L-glutaminate is C45H56O16N26, structural formula is：
2. a kind of TMeQ as claimed in claim 1 [6] and D, the preparation method of L-glutaminate super molecular complex, its feature
It is：It is prepared according to the following steps：
A. TMeQ [6] is used into dissolving with hydrochloric acid, obtains A product；
B. A product are divided into into two parts, it is a to mix with excessive object D-Gln, B product are obtained, the object L- of another and excess
Glutamine mixes, and obtains C product；
C. B product and C product are heated respectively, is stood after heating until there is crystallization, the crystallization in B product is TMeQ [6]-D- paddy ammonia
Amide super molecular complex, the crystallization in C product is TMeQ [6]-L-glutaminate super molecular complex.
3. TMeQ [6] as claimed in claim 2 and D, the preparation method of L-glutaminate super molecular complex, its feature exists
In：It is prepared according to the following steps：
A. TMeQ [6] is used into dissolving with hydrochloric acid, obtains A product；
B. A product are divided into two parts, portion is with the amount ratio of the material of object by TMeQ [6] compounds with object D-Gln
0.8~1.0:3~5 ratio mixing, obtains B product；Another presses the thing of TMeQ [6] compounds and object with object L-glutaminate
The amount ratio of matter is 0.8~1.0:3~5 ratio mixing, obtains C product；After mixing respectively by two portions of mixed liquors at 55~60 DEG C plus
2~3min of heat；
C. 2~3min heating is heated respectively at 55~60 DEG C to B product and C product, stands 11~14 days, until there is crystallization, most
The ratio for respectively obtaining two kinds of stable Subjective and Objective eventually is 1:Crystallization in 1 super molecular complex, i.e. B product is TMeQ [6]-D-
Glutamine super molecular complex, the crystallization in C product is TMeQ [6]-L-glutaminate super molecular complex.
4. a kind of TMeQ as claimed in claim 1 [6] and D, the application of L-glutaminate super molecular complex, its feature exists
In：The super molecular complex is used to recognize D-Gln and L-glutaminate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610995975.1A CN106674236B (en) | 2016-11-12 | 2016-11-12 | A kind of TMeQ [6] and D, L-Glutamine super molecular complex and preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610995975.1A CN106674236B (en) | 2016-11-12 | 2016-11-12 | A kind of TMeQ [6] and D, L-Glutamine super molecular complex and preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106674236A true CN106674236A (en) | 2017-05-17 |
| CN106674236B CN106674236B (en) | 2018-10-09 |
Family
ID=58839601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610995975.1A Active CN106674236B (en) | 2016-11-12 | 2016-11-12 | A kind of TMeQ [6] and D, L-Glutamine super molecular complex and preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106674236B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013091074A1 (en) * | 2011-12-21 | 2013-06-27 | Uvic Industry Partnerships Inc. | Method and array for identifying histone-code-related analytes |
| CN104447768A (en) * | 2013-09-23 | 2015-03-25 | 贵州大学 | Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof |
-
2016
- 2016-11-12 CN CN201610995975.1A patent/CN106674236B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013091074A1 (en) * | 2011-12-21 | 2013-06-27 | Uvic Industry Partnerships Inc. | Method and array for identifying histone-code-related analytes |
| CN104447768A (en) * | 2013-09-23 | 2015-03-25 | 贵州大学 | Cucurbit [7] uril [3] rotaxane as well as preparation method and application thereof |
Non-Patent Citations (5)
| Title |
|---|
| JUN-MING YI ET AL.: "Crystal structures of four host-guest inclusion complexes of α,α’,δ,δ’-tetramethylcucurbit[6] uril and cucurbit[8]uril with some L-amino acids", 《JOURNAL OF MOLECULAR STRUCTURE》 * |
| ZHONG-ZHENG GAO ET AL.: "Host–guest interactions in tetramethyl-cucurbit[6]uril with anti-tuberculosis drug isoniazid", 《INORGANIC CHEMISTRY COMMUNICATIONS》 * |
| 丛航 等: "瓜环对氨基酸的分子识别研究", 《化学学报》 * |
| 范永龙 等: "六元瓜环与D，L-色氨酸配合物的晶体结构分析", 《贵州大学学报( 自然科学版)》 * |
| 陈秀丽 等: "瓜环的研究进展", 《大学化学》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106674236B (en) | 2018-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101811919A (en) | Method for preparing amino acid schiff base metal complexes without solvent | |
| Yang et al. | 1, 1′-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions | |
| CN106748873B (en) | A kind of vitamin B5Mechanical lapping method for preparing solid phase | |
| CN106117253A (en) | The super molecular complex of a kind of melon ring and Amino acid synthesis and preparation method and application | |
| Esteve et al. | Doubly chiral pseudopeptidic macrobicyclic molecular cages: Water-assisted dynamic covalent self-assembly and chiral self-sorting | |
| Fisher et al. | Trivalent Gd-DOTA reagents for modification of proteins | |
| CN106929006A (en) | A kind of identification cysteine and homocysteine fluorescence probe and its preparation and application with naphthalimide as parent nucleus | |
| CN103626697B (en) | A kind of preparation method of the cyanopyridine of 2 chlorine, 4 trifluoromethyl 3 | |
| CN105601528A (en) | Molecular tweezer compound with ent-beyerane diterpene as chiral arm, and preparation method and application thereof | |
| CN103351392B (en) | The product of the symmetrical hexa-atomic melon ring synthetic method of prestox and synthesis | |
| Rajesh et al. | Characterization of a meso-chiral isomer of a hexanuclear Cu (II) cage from racemization of the L-alanine Schiff base | |
| CN106674236B (en) | A kind of TMeQ [6] and D, L-Glutamine super molecular complex and preparation method and application | |
| CN115261015B (en) | N is detected based on ICT principle 2 H 4 And Cu 2+ Double-channel fluorescent probe of (2), and preparation method and application thereof | |
| CN100516025C (en) | Method for synthesizing D-norvaline using n-pentanoic acid | |
| CN108329276A (en) | Hete rocyclic derivatives and its preparation and use | |
| CN111349121A (en) | Cobalt carbonyl complex and preparation method thereof | |
| CN104151170A (en) | 4-nitrophenethylamine hydrochloride and preparation method thereof | |
| CN105481780B (en) | 2- aminopyrimidine is the 5 FU 5 fluorouracil pharmaceutical co-crystals and its preparation method and application of presoma | |
| JP2018104312A (en) | Imidazopyrroloquinoline salt and method for producing the same, and pharmaceutical, cosmetic and food | |
| CN105175400A (en) | Preparation method of Afatinib intermediate | |
| CN106632238A (en) | Thiacalix [4] arene mono-substituted amine Schiff base derivative and synthesis method thereof | |
| CN106674235B (en) | A kind of TMeQ [6] and D, Serine super molecular complex and preparation method and application | |
| CN106674258B (en) | A kind of TMeQ [6] and D, l-methionine super molecular complex and preparation method and application | |
| CN105384744B (en) | Four (trifluoro ethoxy) phthalocyanine europium complexes and its preparation method and application | |
| WO2018178439A1 (en) | Method for the synthesis of 9,10-bis(chloromethyl)anthracene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |