Home » Peptide Services » Peptoid Synthesis
peptoid synthesis

Peptoid Synthesis Service




Peptide drugs are a rapidly growing class of therapeutics. However, the peptide drug discovery has been hampered by its inherent characteristics: low stability due to susceptibility to enzymatic digestion, low target specificity because of high conformational flexibility, low hydrophobicity and the lack of specific transportation systems. In order to overcome these disadvantages of peptide, GenScript has developed an innovative Peptoid Synthesis (SC1559) service to meet the increasing needs in drug target discovery and lead structure discovery research.


Peptoids, or poly-N-substituted glycines, are a class of peptidomimetics whose side chains are appended to the nitrogen atom of the peptide backbone rather than to the α-carbons (as they are in amino acids). In native peptides, R group represents 20 different substitutions for specific amino acids, while in peptoids, the selection of R groups can be much wider and potentially unlimited.

peptoid vs peptide
Fig.1 Structural comparison between peptide and peptoid
  • Services Features
  • Synthesis Method
  • Case Study

Key Features (Peptoid VS. Peptide):

  • More stable: Peptoids are less susceptible to degradation in vivo than peptides.
  • More choices: Peptoids are well suited for combinatorial approaches to drug discovery because large libraries can be synthesized easily from readily available primary amines.
  • More cost-effective and time-efficient: Major advances in screening methodology have allowed peptoid libraries of hundreds of thousands of compounds to be mined inexpensively and quickly for highly specific protein-binding.
  • Higher market potential: The features of peptoids make them a class of pharmacological agents with great potential.

Service Specifications:

Peptoid Synthesis (Cat. No.: SC1559)
  • 20 different residues available, more in development
  • Peptoid length up to 20 residues
  • Peptoid purity from crude to >98%
  • Peptoid quantity up to 500 mg
  • Available modifications: Acetylation, Amidation, Biotin, FAM, FITC, TMR labeling
  • MS, HPLC, and COA provided for each peptoid
  • 2-6 weeks turnaround time, depending on the length and quantity of ordered peptoid
Current Available Peptoid Side Chain

Side Chain Name
Abbreviation
Structural Formula
Methylamine
NAla
Ethylamine
NAbu
n-propylamine
Nnpa
Isopropylamine
NVal
n-butylamine
Nnba
Sec-butylamine
NIle
Isobutylamine
NLeu
Benzylamine
NPhe
β-phenylethylamine
Npea
α-methylbenzylamine
Nmba
2-(methylthio)ethylamine
NMet
3-Methoxypropylamine
Nmpa
N-Boc-1,4-Diaminobutane
NLys
4-methoxyphenethylamine
Nmpe
3,4-Dimethoxybenzylamine
Ndmb
(S)-(+)-Tetrahydrofurfurylamine
Nffa
Piperonylamine
Npip
4-(2-Aminoethyl)benzenesulfonamide
Nbsa
Tert-butylamine
Ntbu
diisopropylamine
Ndip

Delivery Specifications:

The typical delivery package consists of lyophilized peptoids of required sequence, purity, quantity and associated QC reports. Every step of peptoid synthesis is subject to GenScript's stringent quality control.

Peptoid Synthesis Method

The synthesis of a peptoid can be achieved through two methods: monomer and submonomer.

Monomer method: This method is very similar to solid phase synthesis of peptide with the exception that all the protected monomers for peptoid synthesis need to be synthesized first, where the synthesis of every Nα-protected monomer is tedious and time-consuming.

synthesis of peptoid monomers
Fig.2 Synthesis of peptoid monomers

Submonomer method: This method eliminates the need of Nα-protected monomers. Each residue is installed in two steps: acylation followed by nucleophilic displacement. The submonomer approach allows the use of any commercially available or synthetically accessible amine that has great potential for combinatorial chemistry. In the acylation step a haloacetic acid, typically bromoacetic acid, is activated by diisopropylcarbodiimide reacting with the amine of the previous residue. In the displacement step (a classical SN2 reaction), an amine displaces the bromide to form an N-substituted glycine residue. This approach has greater advantages over the monomer approach and has been widely applied to peptoid library construction. We currently apply the Submonomer method for peptoid synthesis.

Submonomer peptoids synthesis
Fig.3 Schematics of peptoid synthesis by submonomer method

Case Study

With proven technical capability and state-of-the-art in-house instruments and technologies, we have successfully synthesized many peptoids.

Sequence: Npip-NVal-Npa-NIle-NLeu-Nnba-Nmba-Ndmb-Nmpe-NIle-Npea-Ndmb-NPhe-NVal-NAla-Nea-NLeu-NAla-NPhe-Nnba-Npa
Structure:
Length: 21 residues
Purity: 98.3%
Theoretical MW: 2733.37
Observed MW: 2732.8
MS result checked by ESI:

HPLC result checkedy by RP-HPLC, C18 column:


Quotations and Ordering:

To request a quotation or order, please download and complete the Order Form and send it to us by email or fax. You can also submit PO/credit card information by phone or via our Secure Web Server

We accept POs and major credit cards (credit card order). A 7% New Jersey sales tax will be applied to orders shipped to New Jersey. Your credit card will be billed under "GenScript USA Inc." Click here to download our credit reference form. For international orders, we must apply the full charge at the time the order is placed. In the unlikely event that any given order cannot be filled, our guarantee will take the form of a full refund.