Fmoc-β-MeSer(OtBu)-OH Protected Amino Acid FAQ
Fmoc-β-MeSer(OtBu)-OH Protected Amino Acid FAQ
(S)-3-(((9H-Fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid is a specialized Fmoc-protected oxazolidine amino acid building block designed for use in solid-phase peptide synthesis (SPPS), offering orthogonal protection of the backbone nitrogen and side-chain hydroxyl via a cyclic acetonide-type constraint.
- Product SKU
- F1539871
- Reference Item Number
- BD01789336
- Chemical Class
- Fmoc-protected oxazolidine amino acid
- Stereochemistry
- (S)-configuration at the oxazolidine C-4 position
- Primary Application
- Solid-phase peptide synthesis (SPPS) building block
- Fmoc Removal Condition
- 20% piperidine in DMF (standard SPPS conditions)
What Is (S)-3-(((9H-Fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic Acid?
(S)-3-(((9H-Fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid (SKU F1539871) is a cyclic, dual-protected amino acid derivative widely employed in Fmoc-based solid-phase peptide synthesis. The molecule incorporates a 9-fluorenylmethoxycarbonyl (Fmoc) group on the ring nitrogen, while the nitrogen and the adjacent oxygen are simultaneously constrained within a 2,2-dimethyloxazolidine ring, effectively protecting the side-chain hydroxyl as an acetonide equivalent.
This compound is commonly used as a constrained surrogate or analogue for serine or threonine residues, and can facilitate the incorporation of beta-hydroxy amino acid motifs into peptide sequences while suppressing unwanted side reactions such as epimerization and diketopiperazine formation during chain elongation.
How Is This Compound Used in Solid-Phase Peptide Synthesis?
In Fmoc SPPS, this building block is coupled to the growing resin-bound peptide chain using standard amide-bond-forming reagents such as HATU, HBTU, or DIC/Oxyma in the presence of a base such as DIPEA. The Fmoc group is removed between each coupling cycle using 20% piperidine in DMF, exposing the free amine for the next coupling step.
The 2,2-dimethyloxazolidine ring serves as an acid-labile protecting group for the side-chain hydroxyl. Upon global deprotection with trifluoroacetic acid (TFA)-based cocktails at the end of synthesis, the oxazolidine ring opens to reveal the free beta-hydroxy amino acid residue within the final peptide. Researchers should verify that their specific deprotection conditions are compatible with all other protecting groups present in the sequence.
Because the ring constrains the backbone nitrogen, this residue may influence local conformation in the assembled peptide; this property can be exploited in the design of conformationally restricted peptide analogues.
Storage, Handling, and Stability
As with most Fmoc-protected amino acid building blocks, F1539871 should be stored in a cool, dry environment away from moisture and light. Exposure to prolonged humidity can promote hydrolysis of the Fmoc carbamate linkage, leading to premature deprotection. It is advisable to store the compound under inert atmosphere (nitrogen or argon) if the container will be opened repeatedly.
Solutions of this compound in polar aprotic solvents such as DMF or NMP are typically prepared fresh before use. Operators should consult the product Safety Data Sheet (SDS) for specific hazard information, personal protective equipment (PPE) requirements, and waste-disposal guidelines before handling this reagent.
If long-term stability data or specific shelf-life information is required, please contact Aladdin Scientific technical support for the most current certificate of analysis (CoA) details.
Ordering and Availability
This product is available from Aladdin Scientific under SKU F1539871, with the reference item number BD01789336. To place an order, log in to your Aladdin account, search by SKU or product name, and add the desired quantity to your cart. For bulk quantities, custom packaging, or institutional procurement inquiries, please contact our sales team directly.
Availability may vary by region. Customers should verify current stock status and lead times on the Aladdin Scientific website or by contacting customer service. Pricing, promotions, and quantity discounts are subject to change; please refer to the current online catalog for up-to-date information.
Frequently asked questions
What is the role of the 2,2-dimethyloxazolidine ring in this compound?
The 2,2-dimethyloxazolidine ring simultaneously protects the backbone nitrogen and side-chain hydroxyl of the amino acid by forming a cyclic acetonide-type structure. This dual protection prevents side reactions during SPPS coupling steps and is cleaved under acidic global deprotection conditions (e.g., TFA) to reveal the free beta-hydroxy amino acid residue in the final peptide.
How should I remove the Fmoc group from F1539871 during SPPS?
The Fmoc group is removed using standard SPPS conditions: treatment with 20% piperidine in DMF for one or two cycles (typically 5 minutes followed by 15 minutes). This base-mediated beta-elimination cleaves the Fmoc carbamate and liberates the free amine for the next coupling step. The dibenzofulvene byproduct can be monitored by UV absorbance to confirm complete deprotection.
Is F1539871 compatible with common SPPS coupling reagents?
Yes, this Fmoc-oxazolidine building block is generally compatible with standard SPPS coupling reagents including HATU, HBTU, HCTU, and DIC/Oxyma combinations in DMF or NMP, with a hindered base such as DIPEA. Users are advised to optimize coupling time and equivalents for sterically demanding sequences, and to confirm coupling efficiency by ninhydrin or chloranil test before proceeding to the next cycle.
What analytical methods can be used to characterize F1539871?
This compound can be characterized by standard analytical techniques including proton and carbon NMR spectroscopy to confirm structure and stereochemistry, LC-MS or HRMS for molecular weight confirmation, and HPLC for purity assessment. Optical rotation measurement can verify the (S)-stereochemical assignment. Aladdin Scientific provides a certificate of analysis (CoA) with purity and identity data for each lot.
Can this compound be used for the synthesis of glycopeptides or other modified peptides?
This building block is primarily designed to introduce beta-hydroxy amino acid residues into peptide sequences, making it relevant to the synthesis of peptides bearing serine or threonine surrogates with conformational constraints. Its utility in glycopeptide synthesis would depend on subsequent selective deprotection and glycosylation steps; researchers should evaluate compatibility with their specific synthetic strategy and consult the relevant literature for precedents.
References
- Fields, G. B.; Noble, R. L. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids. International Journal of Peptide and Protein Research, 1990, 35(3), 161–214.
- Carpino, L. A.; Han, G. Y. The 9-fluorenylmethoxycarbonyl amino-protecting group. Journal of Organic Chemistry, 1972, 37(22), 3404–3409.
- Aladdin Scientific. Product Certificate of Analysis: (S)-3-(((9H-Fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid, SKU F1539871 (BD01789336).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）