CN109715647A - 用于高温固相肽合成的原位溶剂回收方法 - Google Patents
用于高温固相肽合成的原位溶剂回收方法 Download PDFInfo
- Publication number
- CN109715647A CN109715647A CN201780053940.9A CN201780053940A CN109715647A CN 109715647 A CN109715647 A CN 109715647A CN 201780053940 A CN201780053940 A CN 201780053940A CN 109715647 A CN109715647 A CN 109715647A
- Authority
- CN
- China
- Prior art keywords
- deprotection
- method described
- conjugate solution
- peptide synthesis
- previous
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000010647 peptide synthesis reaction Methods 0.000 title claims abstract description 13
- 239000002904 solvent Substances 0.000 title description 13
- 238000011084 recovery Methods 0.000 title description 2
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 30
- 238000005859 coupling reaction Methods 0.000 claims abstract description 21
- 238000010168 coupling process Methods 0.000 claims abstract description 20
- 230000008878 coupling Effects 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 15
- 239000007790 solid phase Substances 0.000 claims abstract description 13
- 150000001413 amino acids Chemical class 0.000 claims abstract description 12
- 230000004913 activation Effects 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims description 9
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000003235 pyrrolidines Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 108010004034 stable plasma protein solution Proteins 0.000 description 2
- -1 2- cyano -2- (oxyimino) acetic acid Chemical class 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 241001474728 Satyrodes eurydice Species 0.000 description 1
- KPFBUSLHFFWMAI-HYRPPVSQSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-6-formyl-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=C(C=O)C[C@H]2[C@@H]2CC[C@](OC(C)=O)(C(C)=O)[C@]21C KPFBUSLHFFWMAI-HYRPPVSQSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CSHFHJNMIMPJST-HOTGVXAUSA-N methyl (2s)-2-[[(2s)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate Chemical compound NCC(=O)NCC(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)OC)CC1=CC=CC=C1 CSHFHJNMIMPJST-HOTGVXAUSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/045—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers using devices to improve synthesis, e.g. reactors, special vessels
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/047—Simultaneous synthesis of different peptide species; Peptide libraries
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662383397P | 2016-09-03 | 2016-09-03 | |
| US62/383,397 | 2016-09-03 | ||
| USPCT/US2016/058181 | 2016-10-21 | ||
| PCT/US2016/058181 WO2017070512A1 (en) | 2015-10-23 | 2016-10-21 | Improvements in solid phase peptide synthesis |
| US15/299,931 | 2016-10-21 | ||
| US15/299,931 US10125163B2 (en) | 2015-10-23 | 2016-10-21 | Solid phase peptide synthesis |
| US15/490,090 US10239914B2 (en) | 2015-10-23 | 2017-04-18 | In-situ solvent recycling process for solid phase peptide synthesis at elevated temperatures |
| US15/490,090 | 2017-04-18 | ||
| PCT/US2017/028254 WO2018044356A1 (en) | 2016-09-03 | 2017-04-19 | In-situ solvent recycling process for solid phase peptide synthesis at elevated temperatures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109715647A true CN109715647A (zh) | 2019-05-03 |
Family
ID=61301481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201780053940.9A Pending CN109715647A (zh) | 2016-09-03 | 2017-04-19 | 用于高温固相肽合成的原位溶剂回收方法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP3507299B1 (enExample) |
| JP (1) | JP2019530659A (enExample) |
| CN (1) | CN109715647A (enExample) |
| CA (1) | CA3034810C (enExample) |
| DK (1) | DK3507299T3 (enExample) |
| WO (1) | WO2018044356A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE49961E1 (en) | 2016-10-21 | 2024-05-07 | Cem Corporation | Solid phase peptide syntheses |
| EP4551587A1 (en) * | 2022-09-16 | 2025-05-14 | CEM Corporation | Peptide synthesis processes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140275481A1 (en) * | 2013-03-15 | 2014-09-18 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| CN108368152A (zh) * | 2015-10-23 | 2018-08-03 | Cem有限公司 | 固相肽合成中的改进 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040238794A1 (en) * | 2003-05-30 | 2004-12-02 | Karandikar Prashant G. | Microwave processing of composite bodies made by an infiltration route |
| US7393920B2 (en) * | 2003-06-23 | 2008-07-01 | Cem Corporation | Microwave-assisted peptide synthesis |
| US7902488B2 (en) * | 2003-06-23 | 2011-03-08 | Cem Corporation | Microwave-assisted peptide synthesis |
| WO2006026184A2 (en) * | 2004-08-20 | 2006-03-09 | Washington University | Blood brain barrier permeation peptides |
| US8314208B2 (en) * | 2006-02-10 | 2012-11-20 | Cem Corporation | Microwave enhanced N-fmoc deprotection in peptide synthesis |
| CA2808270A1 (en) * | 2010-08-16 | 2012-02-23 | Cem Corporation | Water soluble solid phase peptide synthesis |
| US8906681B2 (en) * | 2011-08-02 | 2014-12-09 | The Scripps Research Institute | Reliable stabilization of N-linked polypeptide native states with enhanced aromatic sequons located in polypeptide tight turns |
| EP2703073A1 (en) * | 2012-08-31 | 2014-03-05 | Biotage AB | Apparatus and method for solid phase synthesis |
-
2017
- 2017-04-19 CA CA3034810A patent/CA3034810C/en active Active
- 2017-04-19 CN CN201780053940.9A patent/CN109715647A/zh active Pending
- 2017-04-19 WO PCT/US2017/028254 patent/WO2018044356A1/en not_active Ceased
- 2017-04-19 JP JP2019511957A patent/JP2019530659A/ja active Pending
- 2017-04-19 DK DK17847113.2T patent/DK3507299T3/da active
- 2017-04-19 EP EP17847113.2A patent/EP3507299B1/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140275481A1 (en) * | 2013-03-15 | 2014-09-18 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| CN108368152A (zh) * | 2015-10-23 | 2018-08-03 | Cem有限公司 | 固相肽合成中的改进 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019530659A (ja) | 2019-10-24 |
| EP3507299A4 (en) | 2020-04-29 |
| DK3507299T3 (da) | 2022-09-05 |
| CA3034810A1 (en) | 2018-03-08 |
| WO2018044356A1 (en) | 2018-03-08 |
| EP3507299A1 (en) | 2019-07-10 |
| CA3034810C (en) | 2023-09-05 |
| EP3507299B1 (en) | 2022-07-27 |
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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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190503 |
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| RJ01 | Rejection of invention patent application after publication |