JP2006504786A5 - - Google Patents
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- Publication number
- JP2006504786A5 JP2006504786A5 JP2004550127A JP2004550127A JP2006504786A5 JP 2006504786 A5 JP2006504786 A5 JP 2006504786A5 JP 2004550127 A JP2004550127 A JP 2004550127A JP 2004550127 A JP2004550127 A JP 2004550127A JP 2006504786 A5 JP2006504786 A5 JP 2006504786A5
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- mobile phase
- proline
- phase modifier
- lipopeptide
- 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
- 238000000034 method Methods 0.000 description 11
- 229940024606 amino acid Drugs 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 8
- 239000003607 modifier Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 amino acid ester Chemical class 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 108010028921 Lipopeptides Proteins 0.000 description 4
- 229960002429 proline Drugs 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 2
- 150000008574 D-amino acids Chemical class 0.000 description 2
- 229930182820 D-proline Natural products 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229930182821 L-proline Natural products 0.000 description 2
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004473 Threonine Substances 0.000 description 2
- DQXPFAADCTZLNL-FXDJFZINSA-N pneumocandin B0 Chemical group C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CC(N)=O)=CC=C(O)C=C1 DQXPFAADCTZLNL-FXDJFZINSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229960002898 threonine Drugs 0.000 description 2
- 108010020326 Caspofungin Proteins 0.000 description 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 description 1
- 229930182818 D-methionine Natural products 0.000 description 1
- KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 description 1
- 229930182831 D-valine Natural products 0.000 description 1
- 108010013198 Daptomycin Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 150000008575 L-amino acids Chemical group 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- 108010021062 Micafungin Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- JYIKNQVWKBUSNH-WVDDFWQHSA-N caspofungin Chemical compound C1([C@H](O)[C@@H](O)[C@H]2C(=O)N[C@H](C(=O)N3CC[C@H](O)[C@H]3C(=O)N[C@H](NCCN)[C@H](O)C[C@@H](C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N2)[C@@H](C)O)=O)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@H](O)CCN)=CC=C(O)C=C1 JYIKNQVWKBUSNH-WVDDFWQHSA-N 0.000 description 1
- 229960003034 caspofungin Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- DOAKLVKFURWEDJ-QCMAZARJSA-N daptomycin Chemical compound C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N DOAKLVKFURWEDJ-QCMAZARJSA-N 0.000 description 1
- 229960005484 daptomycin Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229960002159 micafungin Drugs 0.000 description 1
- PIEUQSKUWLMALL-YABMTYFHSA-N micafungin Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N[C@@H]2C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C2)[C@H](O)CC(N)=O)[C@H](O)[C@@H](O)C=2C=C(OS(O)(=O)=O)C(O)=CC=2)[C@@H](C)O)=O)=NO1 PIEUQSKUWLMALL-YABMTYFHSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- PMMYEEVYMWASQN-IUYQGCFVSA-N trans-4-hydroxy-D-proline Chemical compound O[C@@H]1CN[C@@H](C(O)=O)C1 PMMYEEVYMWASQN-IUYQGCFVSA-N 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42235602P | 2002-10-30 | 2002-10-30 | |
| PCT/US2003/033978 WO2004042350A2 (en) | 2002-10-30 | 2003-10-24 | Using amines or amino acids as mobile phase modifiers in chromatography |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006504786A JP2006504786A (ja) | 2006-02-09 |
| JP2006504786A5 true JP2006504786A5 (enExample) | 2010-05-13 |
| JP4549862B2 JP4549862B2 (ja) | 2010-09-22 |
Family
ID=32312493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004550127A Expired - Fee Related JP4549862B2 (ja) | 2002-10-30 | 2003-10-24 | クロマトグラフィーにおける移動相改質剤としてのアミンまたはアミノ酸の使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7241866B2 (enExample) |
| EP (1) | EP1558354B1 (enExample) |
| JP (1) | JP4549862B2 (enExample) |
| AT (1) | ATE457798T1 (enExample) |
| AU (1) | AU2003284163A1 (enExample) |
| CY (1) | CY1110296T1 (enExample) |
| DE (1) | DE60331338D1 (enExample) |
| DK (1) | DK1558354T3 (enExample) |
| ES (1) | ES2342772T3 (enExample) |
| PT (1) | PT1558354E (enExample) |
| SI (1) | SI1558354T1 (enExample) |
| WO (1) | WO2004042350A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPS264302A0 (en) * | 2002-05-29 | 2002-06-20 | Neopraxis Pty Ltd | Implantable bladder sensor |
| CN103936837B (zh) * | 2014-02-14 | 2016-05-25 | 博瑞生物医药泰兴市有限公司 | 一种提纯纽莫康定b0的方法 |
| US10383550B2 (en) * | 2014-07-17 | 2019-08-20 | Elwha Llc | Monitoring body movement or condition according to motion regimen with conformal electronics |
| CN105001305A (zh) * | 2015-04-29 | 2015-10-28 | 利穗科技(苏州)有限公司 | 利用层析技术提取高纯度达托霉素的方法 |
| CN108250274A (zh) * | 2016-12-28 | 2018-07-06 | 浙江华谱新创科技有限公司 | 米卡芬净高效分离纯化方法 |
| BR112022013481A2 (pt) * | 2020-01-08 | 2022-09-13 | Regeneron Pharma | Uso de aminoácidos para aumentar o sinal em análises espectro de massa |
| CN111925421B (zh) * | 2020-07-02 | 2022-05-10 | 北大方正集团有限公司 | 一种从发酵液中提取纽莫康定b0的方法与应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4812442A (en) * | 1984-05-29 | 1989-03-14 | Merck & Co., Inc. | Tripeptide renin inhibitors |
| IT1190433B (it) | 1985-12-11 | 1988-02-16 | Prodotti Antibiotici Spa | Peptidi correlati al lisozima |
| US5194377A (en) | 1989-06-30 | 1993-03-16 | Merck & Co., Inc. | Antibiotic agent |
| US5202309A (en) | 1989-06-30 | 1993-04-13 | Merck & Co., Inc. | Antibiotic cyclopeptide fermentation product |
| GB9508195D0 (en) * | 1995-04-20 | 1995-06-07 | Univ British Columbia | Novel biologically active compounds and compositions,their use and derivation |
| WO1998041489A1 (en) * | 1997-03-18 | 1998-09-24 | Chiral Technologies, Inc. | Chiral separations of amino acids |
| JP3780638B2 (ja) | 1997-06-27 | 2006-05-31 | 東ソー株式会社 | 分離法及びこれを用いた装置 |
-
2003
- 2003-10-24 AT AT03776553T patent/ATE457798T1/de active
- 2003-10-24 EP EP03776553A patent/EP1558354B1/en not_active Expired - Lifetime
- 2003-10-24 JP JP2004550127A patent/JP4549862B2/ja not_active Expired - Fee Related
- 2003-10-24 AU AU2003284163A patent/AU2003284163A1/en not_active Abandoned
- 2003-10-24 DK DK03776553.4T patent/DK1558354T3/da active
- 2003-10-24 DE DE60331338T patent/DE60331338D1/de not_active Expired - Lifetime
- 2003-10-24 SI SI200331785T patent/SI1558354T1/sl unknown
- 2003-10-24 PT PT03776553T patent/PT1558354E/pt unknown
- 2003-10-24 WO PCT/US2003/033978 patent/WO2004042350A2/en not_active Ceased
- 2003-10-24 US US10/526,301 patent/US7241866B2/en not_active Expired - Fee Related
- 2003-10-24 ES ES03776553T patent/ES2342772T3/es not_active Expired - Lifetime
-
2010
- 2010-05-14 CY CY20101100422T patent/CY1110296T1/el unknown
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