Mal-beta-Ala-OSu is a malonyl-β-alanine N-hydroxysuccinimide ester (OSu), functioning as an amino acid derivative in which the β-alanine carboxyl group is activated as an N-hydroxysuccinimide ester while the side chain bears a malonyl substituent. The molecule contains an activated ester carbonyl, an N-hydroxysuccinimide leaving group, and an amino functionality consistent with a β-amino acid framework, with stereochemistry not specified in the provided name. Mal-beta-Ala-OSu is used in peptide chemistry and chemical biology workflows as an acylating reagent to introduce the β-alanine-malonyl motif onto nucleophilic amines or other functional groups during the preparation of labeled conjugates, crosslinking handles, or more complex amino acid and peptide intermediates.
CAT No: CP25897
CAS No:55750-62-4
Chemical Name:3-(Maleimido)propionic acid N-succinimidyl ester, N-Maleoyl-beta-alanine N-hydroxysuccinimide ester
Mal-beta-Ala-OSu is a β-alanine derivative bearing a maleoyl (Mal) substituent and an activated N-hydroxysuccinimide ester (OSu) functionality, combining an amino acid backbone with a highly reactive carboxylate leaving group. The stereochemical outcome is governed by the β-amino acid framework, while the maleoyl motif introduces an electron-deficient alkene capable of undergoing Michael-type reactivity under appropriate conditions. The OSu ester is predisposed to acyl transfer to nucleophiles such as primary amines, enabling rapid formation of amide linkages without requiring separate coupling reagents. The resulting electrophile-nucleophile compatibility makes Mal-beta-Ala-OSu a research-grade intermediate for constructing amino acid conjugates, peptide-like linkages, and functionalized scaffolds while maintaining clear downstream synthetic handles for further transformation.
1. Peptide Coupling Chemistry
Mal-beta-Ala-OSu is applied in peptide synthesis workflows where activated carboxylate chemistry is needed for rapid amide bond formation. The OSu ester activates the carboxyl functionality of the β-alanine unit, supporting coupling to protected or unprotected amines under conditions compatible with amino acid derivative handling. The maleoyl substituent provides an additional reactive element that can be carried through coupling steps and later used for conjugation, crosslinking, or scaffold elaboration. The β-amino acid geometry also allows incorporation into peptide building block strategies aimed at generating β-substituted linkages and peptidomimetic motifs. Mal-beta-Ala-OSu thus functions as an amino acid-based intermediate that bridges protected amino acid synthesis concepts with direct coupling chemistry for downstream peptide analog construction.
2. Bioconjugation Platforms
Mal-beta-Ala-OSu is suitable for chemical biology and bioconjugation applications requiring controlled attachment of an amino acid-derived linker to biomolecular nucleophiles. The N-hydroxysuccinimide ester reacts readily with lysine ε-amines and other primary amines to form stable amide conjugates, while the maleoyl alkene can serve as a secondary reactive handle for subsequent conjugation steps or modular assembly. The β-alanine spacer contributes to defined linker length and can influence conjugate solubility and steric presentation relative to biomolecular surfaces. The combination of an acylating OSu group and a maleoyl electrophile supports sequential or orthogonal functionalization strategies where the amide formation step precedes alkene-based modification. Mal-beta-Ala-OSu enables the preparation of amino acid-derived conjugates used in labeling, probe construction, and biomolecule modification studies.
3. Peptidomimetic Linker Design
Mal-beta-Ala-OSu is used in peptidomimetic and molecular design efforts where amino acid-derived electrophiles help build constrained or functionalized scaffolds. The β-alanine core provides a stereochemically defined backbone element, while the OSu ester supports conversion into amide-linked intermediates that mimic peptide bond connectivity. The maleoyl moiety introduces an unsaturated, electron-deficient motif that can participate in Michael-type additions or further derivatization to tune binding-site chemistry in synthetic analogs. The ability to transform the OSu group into an amide allows incorporation into larger chain assemblies, including β-peptide mimics and linker-bearing oligomers. Mal-beta-Ala-OSu therefore serves as a chiral amino acid intermediate conceptually aligned with peptide science, enabling construction of functional peptidomimetic architectures for structure-focused studies.
4. Process Chemistry Intermediate Preparation
Mal-beta-Ala-OSu is relevant to process chemistry and fine chemical synthesis as an activated amino acid derivative intermediate designed for reagent-efficient acyl transfer. The OSu ester form concentrates reactivity into a single electrophilic site, which can simplify downstream steps by reducing the need for separate coupling reagents when preparing amide-linked products. The maleoyl substituent provides a chemically persistent functionality that can be carried through intermediate formation and then consumed in later transformations, supporting modular manufacturing routes. The compound's defined amino acid-based structure also supports consistent stoichiometric behavior in industrial intermediate preparation for linker, conjugate, and scaffold synthesis. Mal-beta-Ala-OSu can be employed as a controlled electrophile in industrial chemical manufacturing where amino acid derivatization and subsequent functional group conversion are integrated into a multi-step synthetic sequence.
5. Analytical Research Standards
Mal-beta-Ala-OSu is applied in analytical research contexts where labeled or structurally defined amino acid derivatives are needed as standards and reference materials. The OSu ester enables selective formation of amide derivatives with chosen nucleophiles, allowing generation of conjugate standards that reflect the β-alanine linkage and maleoyl functionality. The maleoyl alkene provides a distinct chemical signature that can improve detectability and confirm structural integrity after derivatization steps. The β-amino acid framework supports reproducible derivatization patterns useful for method development in LC-MS and related analytical workflows targeting amino acid conjugates and linker-containing species. Mal-beta-Ala-OSu thus functions as an amino acid derivatization reagent that supports downstream analytical standard preparation and structural verification in research laboratories and industrial quality control environments.
1. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy
2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
5. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More