asp peptide labile under acidic conditions - Glu amino acid Asp Understanding Asp Peptides: A Comprehensive Exploration of Aspartic Acid in Peptide Chemistry

Cysteine Aspartic acid, often abbreviated as Asp or D, is a fundamental α-amino acid crucial for protein biosynthesisMolecular formula: C8H12N2O7. Average mass: 248.191. Monoisotopic mass: 248.064451. ChemSpider ID: 295009. 0 of 2 defined stereocenters. Download .mol. When incorporated into peptide chains, it plays a significant role in various biological processes and chemical reactions作者：K Aki·2016·被引用次数：12—Kinetic analysis showed how tough the uncommon D-β-Aspresidue was against thepeptidebond cleavage as compared to natural L-α-Asp. Differences .... This exploration delves into the multifaceted world of asp peptides, examining their structure, properties, applications, and the specific challenges associated with their synthesis and handling.

The Fundamental Role of Aspartic Acid in Peptides

As one of the 20 standard amino acids, aspartic acid possesses a carboxylic acid side chain, making it an acidic amino acid.作者：L Meng·2025·被引用次数：4—In molecular design, theAsp–peptide adapterswere introduced innovatively, which is like a squirrel tail structure that endows the probe with better biological ... This acidic nature influences the overall charge and behavior of peptides containing Asp. The ionic form of aspartic acid is known as aspartate. In the realm of peptide synthesis, the careful placement and handling of aspartic acid residues are paramount to achieving desired outcomes and avoiding unwanted side reactions.Giving the FAP-Targeted Radioligand a “Squirrel Tail”

Exploring Specific Asp Peptide Structures and Their Significance

The versatility of aspartic acid in peptide sequences is evident in the numerous dipeptides, tripeptides, and longer peptides that have been studied.ACE-Inhibitory Activity and Structural Properties of Peptide ... For instance, Asp-Asp (also known as asp-asp with CAS number 58471-53-7) is a simple dipeptide composed of two aspartic acid residues.Fmoc-Asp(OtBu)-OH [71989-14-5] Its molecular formula is C8H12N2O7, with an average mass of 248.191.作者：L Meng·2025·被引用次数：4—In molecular design, theAsp–peptide adapterswere introduced innovatively, which is like a squirrel tail structure that endows the probe with better biological ... Another example is Asp-Val, a dipeptide formed from L-alpha-aspartyl and L-valine residues, which has been identified to play a role as a metaboliteAspartic acid. Asp-His is another dipeptide composed of L-aspartic acid and L-histidine, also with a recognized role as a metabolite.

Beyond dipeptides, tripeptides featuring aspartic acid are also of interest. Glu-Asp-Asp is described as a tripeptide composed of one L-glutamic acid and two L-aspartic acid units joined by peptide linkages. The pentapeptide Asp-Asp-Asp-Asp-Asp highlights the potential for repeating aspartic acid units in a peptide sequence, often synthesized for research purposesCAS Number: 1392278-76-0. Synonyms: cyclic[Cys-Arg-Gly-Asp-Lys-Gly-Pro-Asp-Cys],Internalizing Arginine-Glycine-Aspartic Acid Peptide. Purity: ≥95%..

RGD (Arg-Gly-Asp) Peptides: A Prominent Family

A particularly significant class of peptides containing aspartic acid are those with the RGD (Arg-Gly-Asp) sequence. These RGD peptides represent a cell adhesion motif that can mimic cell adhesion proteins and bind effectively to integrins. Their ability to interact with integrins makes them valuable tools in cell adhesion studies and has led to the development of high-purity RGD (Arg-Gly-Asp) peptides for research applications, including integrin binding inhibition. The repetitive Arg-Gly-Asp (rRGD) peptide has also been explored as a cell-stimulating agent. Furthermore, variations like the Internalizing Arginine-Glycine-Aspartic Acid Peptide (also known by CAS number 1392278-76-0) have emerged, demonstrating the continued innovation in this area. The H-Arg-Gly-Asp-OH peptide is readily available through standard peptide synthesis.

Challenges and Considerations in Asp Peptide Synthesis

The synthesis of peptides containing aspartic acid residues can present unique challenges, primarily due to the propensity of aspartic acid to undergo side reactions, most notably aspartimide formation. The Asp(OtBu) residue, a protected form of aspartic acid, can form an aspartimide under strong basic conditions. This aspartimide can then open to yield either the desired peptide or, problematically, the beta-peptide isomer. This formation of d-aspartyl-peptides can lead to hidden contaminants in purified peptides, as they share identical molecular mass and highly similar physicochemical properties with their correctly formed counterparts.

Research into preventing or mitigating aspartimide formation is ongoingAsp-Asp | C8H12N2O7. For example, studies have focused on strategies for prevention of aspartimide formation during peptide synthesis, particularly within Fmoc-based solid-phase peptide synthesis (Fmoc SPPS). The "Asp-Pro-peptide bond is labile under acidic conditions," which is another factor to consider during synthetic procedures.Asp-based lactam cyclic peptides are considered promising drug candidates. However, using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) for these peptides also ... Efficient methods for peptide ligation have also been developed, such as the technique employing C-terminal Asp(OAllyl) and N-terminal Cys. The design of Asp-based lactam cyclic peptides also holds promise as drug candidates, though their synthesis via Fmoc SPPS requires careful consideration of these potential side reactions.

An interesting facet of this chemistry is the resistance of certain aspartic acid residues to cleavageAsp-Ser-Asp | C11H17N3O9 | CID 14704056 - PubChem - NIH. The d-β-aspartyl residue has demonstrated uncommon high resistance to peptide bond cleavage compared to natural L-α-Asp residues, as revealed by kinetic analysis.

Asp Peptides in Broader Contexts

Beyond specific research applications, aspartic acid itself is a key amino acid with broader implications. Aspartic acid health library resources often detail its physiological rolesCAS 58471-53-7: asp-asp. While critical aspects of peptide hormone abuse in exercise and sports are a concern, the fundamental chemistry of aspartic acid in a peptide context is a distinct and less controversial area of scientific inquiry.Asp-Pro - an overview The development of asp-peptide adapters, described with a "squirrel tail" structure, showcases innovative molecular design for enhancing probe properties in biological applicationsRepetitive Arg‐Gly‐Asp peptide as a cell‐stimulating agent .... The field also explores enzymes designed for specific functions, such as the design of a constitutively active peptide asp.Efficient peptide ligation between allyl-protected Asp and ... ligase.Aspartic Acid - an overview | ScienceDirect Topics

In summary, asp peptides represent a diverse and important area within peptide chemistry. From their fundamental role as building blocks in proteins to their specific applications in drug discovery and biological research, understanding the properties and synthetic challenges associated with aspartic acid in peptide sequences is essential for advancing scientific knowledge and developing new technologies作者：N Kamo·2018·被引用次数：29—An efficient method for peptide ligationbetween C-terminal Asp(OAllyl) and N-terminal Cys has been developed..