The aminolysis of N-hydroxysuccinimide esters. A structure-reactivity study

Cline, Gary W.; Hanna, Samir B.

doi:10.1021/ja00244a035

Cited by 81 publications

(67 citation statements)

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“…[12] This kinetic selectivity also allows selective attachment of lysine-containing peptides through their N-terminal amino group owing to the different basicity of this amino group (pK a % 8) versus that of the lysine side chain (pK a % 11). [11] In the absence of amino groups, conversion of active esters with hydroxy groups is possible, though elevated temperatures and activating agents such as N,N-dimethylaminopyridine may be required.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Functional Polymers by Post‐Polymerization Modification

2008

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Post-polymerization modification is based on the direct polymerization or copolymerization of monomers bearing chemoselective handles that are inert towards the polymerization conditions but can be quantitatively converted in a subsequent step into a broad range of other functional groups. The success of this method is based on the excellent conversions achievable under mild conditions, the excellent functional-group tolerance, and the orthogonality of the post-polymerization modification reactions. This Review surveys different classes of reactive polymer precursors bearing chemoselective handles and discusses issues related to the preparation of these reactive polymers by direct polymerization of appropriately functionalized monomers as well as the post-polymerization modification of these precursors into functional polymers.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Functional Polymers by Post‐Polymerization Modification

2008

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“…The respective reactive polymers poly(N-hydroxy succinimide acrylate) (PNHSA) and poly(N-hydroxy succinimide methacrylate) (PNHSMA) can react with amines in a polymer analogous reaction (also called postpolymerization modification) under very mild reaction conditions, yielding functionalized polyacrylamide or polymethacrylamide derivates. [21][22][23][24] By combining reactive polymers with various amines, functional polymers are now accessible that could not be prepared by the direct polymerization of the respective acrylamide monomers. The conversion of polymeric activates esters with amines is usually quantitative and proceeds (usually) without any side reactions under mild conditions, such as stirring at room temperature.…”

Section: Polymeric Activated Estersmentioning

confidence: 99%

Synthesis of well‐defined polymeric activated esters

Théato

2008

J. Polym. Sci. A Polym. Chem.

276

260

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Monomers bearing an activated ester group can be polymerized under various controlled polymerization techniques, such as ATRP, NMP, RAFT polymerization, or ROMP. Combining the functionalization of polymers via polymeric activated esters with these controlled polymerization techniques generate possibilities to realize highly functionalized polymer architectures. Within this highlight two different research areas of activated esters in polymer science will be discussed: (i) the preparation of defined reactive polymer architectures by controlled polymerization techniques and (ii) the preparation of defined reactive thin films. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 6677–6687, 2008

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“…For applications involving controlled delivery of proteins, CPs are expected to yield hydrogels resilient for dissolution in biological milieu. With RPs, we observed that in vivo release of proteins from NiPAM hydrogels was dependent on M w of NiPAM polymers, where $400 kD polymers gave better retention of the proteins at the site of application [32]. Similarly, in vitro release of cytochrome C (as a model protein) was significantly retarded for high M w polymers in an independent study [30].…”

Section: Thermoreversible Propertiesmentioning

confidence: 91%

“…AcCl, a reagent with a higher electronegative atom on the -C=O, on the other hand, gave readily detectable vinyl peaks under reaction conditions similar to NASI reaction ( Figure 3B, bottom spectrum), indicating more effective derivatization of terminal -NH 2 with AcCl. It was likely that a decrease in electron density of -C=O would have increased the efficiency of the amide condensation [32], since the proposed acylation intermediate bears a net negative charge. Accordingly, all MMA macromers were prepared by the AcCl reaction of the -NH 2 group of the semitelomeric MMA.…”

Section: Preparation Of Mma Macromers With Variable M Nmentioning

confidence: 99%

Hydrogels of Thermoreversible Comb‐Polymers Exhibit Increased Resistance for Dissolution

Jalil

Uludağ

2004

Materialwissenschaft Werkst

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The N-isopropylacrylamide (NiPAM) polymers exhibit thermoreversible properties in aqueous solutions. The resiliency of NiPAM hydrogels is believed to influence the outcome when the polymers are utilized in biomedical applications. To determine the influence of polymer architecture on hydrogel resiliency, polymers of Ni-PAM, methyl methacrylate (MMA) and acrylic acid were synthesized as random polymers and as comb polymers, where MMA was incorporated as side-chains. Random polymers exhibited a Lower Critical Solution Temperature (LCST) that decreased in proportion to MMA content in polymers. The LCST of comb polymers was not dependent on MMA content or the length of MMA side-chain (between 3.0 and 10.1 kD). Whereas low molecular weight ($100 kD) random polymers did not form intact gels, comb-polymers of equivalent molecular weight were capable of forming intact gels. Gel resiliency, as determined by propensity of hydrogels to dissolve upon cooling, was improved when the molecular weight of comb-polymers was increased but the length of the MMA sidebranch did not influence the gel resiliency. We conclude that hydrogel dissolution was dependent on polymer architecture as well as the polymer molecular weight.

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The aminolysis of N-hydroxysuccinimide esters. A structure-reactivity study

Cited by 81 publications

References 0 publications

Synthesis of Functional Polymers by Post‐Polymerization Modification

Synthesis of Functional Polymers by Post‐Polymerization Modification

Synthesis of well‐defined polymeric activated esters

Hydrogels of Thermoreversible Comb‐Polymers Exhibit Increased Resistance for Dissolution

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