Boc-D-alanine N-hydroxysuccinimide ester
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Boc-D-alanine N-hydroxysuccinimide ester

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Category
BOC-Amino Acids
Catalog number
BAT-002704
CAS number
34404-33-6
Molecular Formula
C12H18N2O6
Molecular Weight
286.28
Boc-D-alanine N-hydroxysuccinimide ester
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-D-Ala-OSu
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
149-163 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C12H18N2O6/c1-7(13-11(18)19-12(2,3)4)10(17)20-14-8(15)5-6-9(14)16/h7H,5-6H2,1-4H3,(H,13,18)/t7-/m1/s1
InChI Key
COMUWNFVTWKSDT-SSDOTTSWSA-N
Canonical SMILES
CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C

Boc-D-alanine N-hydroxysuccinimide ester, a versatile chemical reagent widely utilized in synthetic organic chemistry and bioconjugation, boasts a plethora of applications. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a cornerstone in peptide synthesis, Boc-D-alanine N-hydroxysuccinimide ester aids in the amalgamation of amino acids to form peptides. This reagent expertly facilitates the creation of stable amide bonds ensuring the production of high-yield and high-purity peptide products. Its indispensable role lies in the customization of peptides for pharmaceutical and biochemical research ushering in a new era of peptide design and exploration.

Protein Labeling: In the realm of protein chemistry, Boc-D-alanine N-hydroxysuccinimide ester takes the spotlight for its prowess in site-specific protein labeling. Through its interaction with amino groups on proteins, it enables the incorporation of diverse functional groups such as fluorescent tags and biotin. This labeling technique is fundamental in unraveling the intricate web of protein interactions localization and function through a myriad of analytical methods pushing the boundaries of protein research and analysis.

Drug Development: At the forefront of drug innovation, Boc-D-alanine N-hydroxysuccinimide ester plays a pivotal role in prodrug development. By modifying active drug molecules, this ester enhances drug stability solubility and targeted delivery. Once administered these protective groups can be cleaved under physiological conditions releasing the active drug and elevating therapeutic efficacy to new heights. This innovative approach holds promise for revolutionizing drug development and delivery strategies.

Bioconjugation: Enabling groundbreaking advancements in bioconjugation, Boc-D-alanine N-hydroxysuccinimide ester functions as a linchpin for linking biomolecules to various entities. From peptides to proteins, this reagent facilitates the formation of stable covalent bonds leading to the creation of multifunctional bioconjugates with diverse applications. These bioconjugates play a vital role in diagnostics imaging and targeted therapy offering a gateway to cutting-edge biomedical applications and discoveries.

1.Separation of D- and L-amino acids by ion exchange column chromatography in the form of alanyl dipeptides.
Csapó J1, Tóth-Pósfai I, Csapó-Kiss Z. Amino Acids. 1991 Oct;1(3):331-7. doi: 10.1007/BF00814002.
A method of ion exchange column chromatography was developed for the determination of D- and L-amino acids in the form of diastereomeric dipeptide. First the protein containing samples were hydrolyzed with 6 molar hydrochloric acid, then the single amino acids were separated in an LKB automated amino acid analyzer with the LKB fraction collector. Following lyophilization, the single amino acids were transformed into alanyl dipeptides with tertiary-butyloxycarbonil-L-alanine-N-hydroxy-succinimide (t-BOC-L-Ala-ONSu) active ester. The alanyl dipeptides were easily separated from one another and the initial amino acids. Determination of the D- and L-amino acids in this form is relatively accurate and reproducible but takes some time (33-38 min). Accuracy of the determination is satisfactory. The coefficient of variation amounts to 3-5%. The use of the method is suggested to laboratories having an amino acid analyzer and wish to determine D-and L-amino acids in synthetic-amino acids complements, peptides or natural materials.
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