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US 2009/0023926 A1Published application
Trityl Derivatives for Enhancing Mass Spectrometry
OwnerEdwin Mellor Southern, Vladimir Korshun +1inventors
InventorsEdwin Mellor Southern, Vladimir Korshun, Mikhail Sergeevich Shchepinov
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Abstract
The present invention provides a compound of the formula: (IIa); having a reactive functional group M, capable of reacting with a biopolymer, BP, having at least one group capable of reacting with M to form a covalent linkage, to provide a biopolymer derivative of the formula: (IIIa). The biopolymer derivatives of the invention have enhanced ionisability with respect to free 10 biopolymer (Bp) enabling improved analysis of the biopolymer using mass spectrometry. The invention further provides specific examples of compounds formula (IIa), e.g. compounds of formula: (IIa-2a) and (IIa-58a).
Claims13
A compound of formula:
A compound of formula:
A compound of formula:
A compound of formula (IIa):
- where:
- X is a group capable of being cleaved from the a-carbon atom to form an ion of formula (I′)
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- M is independently a reactive functional group;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups Ar1 and Ar2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and Ar2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- and
- q independently=1 or more.
11 more elements
A compound of formula (IIb):
- where:
- X★ is a counter-ion to C★;
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- M is independently a reactive functional group;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups Ar1 and Ar2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and A2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- and
- q independently=1 or more.
11 more elements
An ion of formula (I′):
- where:
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- M is independently a reactive functional group;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups Ar1 and Ar2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and Ar2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- and
- q independently=1 or more.
10 more elements
A solid support of formula (IVai), (IVaii) or (IVaiii):
- where:
- X is a group capable of being cleaved from the a-carbon atom of the compound of formula (II) to form an ion of formula (I′)
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- M is independently a reactive functional group;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups A1 and Ar2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and Ar2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- q independently=1 or more;
- Ss is a solid support;
- C—-SS comprises a cleavable bond between C and SS;
- SS—Ar1 comprises a cleavable bond between Ar1 and SS;
- and
- SS—Ar2 comprises a cleavable bond between Ar2 and SS.
15 more elements
A solid support of formula (IVbii) or (IVbiii):
- where:
- X★, Ar1, Ar2, LM, M, n, m, p, q, SS, C—SS, SS—Ar1 and SS—Ar2 are as defined above.
- X★ is a counter-ion to C★;
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- M is independently a reactive functional group;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups Ar1 and Ar2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and Ar2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- q independently=1 or more;
- SS is a solid support;
- C—SS comprises a cleavable bond between C and SS;
- SS—Ar1 comprises a cleavable bond between Ar1 and SS;
- and
- SS—Ar2 comprises a cleavable bond between Ar2 and SS.
16 more elements
A solid support of formula (IVaiv) or (IVbiv):
- where:
- X is a group capable of being cleaved from the a-carbon atom of the compound of formula (II) to form an ion of formula (I′)
- X★ is a counter-ion to C★;
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- M is independently a reactive functional group;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups Ar1 and Ar2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and Ar2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- q independently=1 or more;
- SS is a solid support;
- M″—SS comprises a bond between M″ and SS;
- and
- M″ is the same as M except that SS is bound to a portion of M which does not form part of the residue of M″ remaining attached to the ion of formula (I′) which residue is produced after reaction of group M″.
15 more elements
A method of forming an ion of formula (I):
- comprising the steps of:
- (i) reacting a compound of the formula (IIa):
- with a biopolymer, BP, having at least one group capable of reacting with M to form a covalent linkage, to provide a biopolymer derivative of the formula (IIIa):
- (ii) cleaving the C—X bond between X and the a-carbon atom of the derivative of formula (IIIa) to form the ion of formula (I);
- where:
- C★ is a carbon atom bearing a single positive charge or a single negative charge;
- X is a group capable of being cleaved from the a-carbon atom to form an ion of formula (I);
- M is independently a group capable of reacting with BP to form the covalent linkage;
- BP′ is independently the biopolymer residue of BP produced on formation of the covalent linkage;
- M′ is independently the residue of M produced on formation of the covalent linkage;
- Ar1 is independently an aromatic group or an aromatic group substituted with one or more A;
- Ar2 is independently an aromatic group or an aromatic group substituted with one or more A;
- optionally wherein (a) two or three of the groups Ar1 and A2 are linked together by one or more L5, where L5 is independently a single bond or a linker atom or group;
- and/or (b) two or three of the groups Ar1 and Ar2 together form an aromatic group or an aromatic group substituted with one or more A;
- A is independently a substituent;
- LM is independently a single bond or a linker atom or group;
- n=0, 1 or 2 and m=1, 2, or 3, provided the sum of n+m=3;
- p independently=1 or more;
- and
- q independently=1 or more.
17 more elements
Dependencies are inferred from the claim text.