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Fmoc-D-Trp(Boc)-OH is an Fmoc-protected D-tryptophan derivative in which the indole nitrogen is protected with Boc. This dual protection is designed for Fmoc solid-phase peptide synthesis, keeping the indole protected through base-mediated Fmoc cycles and removing Boc during acidic final cleavage.
D-Trp is frequently used in stereochemical SAR, conformational studies and protease-stability experiments because it combines a bulky aromatic indole side chain with reversed alpha-carbon configuration. The Boc-protected form should be distinguished from Fmoc-D-Trp-OH because the extra protecting group changes molecular weight and cleavage behavior.
Product Information
| Product Name | Fmoc-D-Trp(Boc)-OH |
| Catalog No. | AS3038 |
| CAS No. | 163619-04-3 |
| Molecular Formula | C31H30N2O6 |
| Molecular Weight | 526.58 g/mol |
| Protecting Groups | Fmoc alpha-amino protection; Boc protection on indole nitrogen |
| Primary Application | D-tryptophan incorporation in Fmoc-SPPS |
Application Scope and Assay Relevance
Primary use: Protected D-tryptophan building block for aromatic peptide SAR, receptor-ligand design and membrane-active peptide optimization.
| Typical in vitro relevance | D-Trp substitutions are used in receptor/tissue pharmacology and in membrane-active peptide design. Relevant assays can include receptor binding, isolated-tissue contraction, antimicrobial MIC, membrane permeabilization, serum/protease stability, hemolysis and cytotoxicity. |
| In vivo relevance | D-Trp-containing angiotensin and oxytocin/vasopressin analogs have been examined in animal pharmacology. As with other D-residues, the effect is positional and should be verified rather than generalized. |
Boc protects the indole nitrogen during synthesis
The indole nitrogen can participate in acid-sensitive side chemistry. Boc protection is commonly used to keep it masked during chain assembly and is removed during final acidic cleavage.
Purchasing and QC Considerations
Confirm CAS 163619-04-3, Boc-protected identity and exact molecular weight before preparing coupling solutions. Reference peptide-synthesis grades also specify enantiomeric purity separately from general assay.
Frequently Asked Questions
What does Boc protect?
Boc protects the D-tryptophan indole nitrogen.
When is Boc removed?
It is normally removed during acidic global cleavage.
Is Fmoc-D-Trp(Boc)-OH the same as Fmoc-D-Trp-OH?
No. The Boc-protected derivative has additional mass and different protecting-group behavior.
Product Documents
A Material Safety Data Sheet (MSDS) is available for this product to support laboratory handling, storage and safety assessment.
Certificates of Analysis (COAs) are batch-specific. Please contact us to request the COA for your product, and we will provide it by email.
Related Technical Resources
See Fmoc-D-Phe-OH for a closely related building block or synthesis resource.
Browse the complete D-Form Amino Acids category or use Alan Scientific's Chemical Peptide Synthesis service for custom peptides containing D-amino acids.