201210-25-5

Basic information

• Product Name: FMOC-D-SER(BSI)-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-T-BUTYLDIMETHYLSILYL-D-SERINE;FMOC-O-T-BUTYLDIMETHYLSILYL-D-SERINE;FMOC-D-SER(TBDMS)-OH;FMOC-D-SER-OH, T-BUTYLDIMETHYLSILYL;FMOC-D-SERINE(BSI)-OH;FMOC-D-SER(BSI)-OH;FMOC-D-SER(TBUME 2SI)-OH;Fmoc-O-tert-butyldimethylsilyl-D-serine
• CAS NO: 201210-25-5
• Molecular Formula: C24H31NO5Si
• Molecular Weight: 441.59
• Mol File: 201210-25-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: FMOC-D-SER(BSI)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-SER(BSI)-OH(201210-25-5)
• EPA Substance Registry System: FMOC-D-SER(BSI)-OH(201210-25-5)

Safety Data

• Hazardous Substances Data: 201210-25-5(Hazardous Substances Data)

Usage

General Description

FMOC-D-SER(BSI)-OH is a chemical compound used in solid-phase peptide synthesis. It is a derivative of the amino acid D-serine, with an FMOC (9-fluorenylmethoxycarbonyl) protecting group attached to the amino group and a BSI (2-bromo-5-sulfanyl-3-iodophenyl) group attached to the side chain hydroxyl group. FMOC-D-SER(BSI)-OH is used in the synthesis of peptides and proteins, where it acts as a building block for the assembly of specific sequences of amino acids. The FMOC protecting group is commonly used to temporarily protect the amine group of the amino acid during the synthesis process, while the BSI group is used to protect the hydroxyl group of serine. The resulting compound is water-soluble and stable, making it suitable for use in peptide synthesis.

Upstream product

• 73724-45-5 (R)-N-(fluoren-9-ylmethoxycarbonyl)serine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 136497-85-3 N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester 
• 1030849-50-3 (S)-allyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)propanoate 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 126027-32-5 O-(tert-butyldimethylsilyl)-L-serine 

Downstream Products

• 1529796-58-4 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-O-(tert.-butyldimethylsilyl)-L-serinyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine 
• 1159428-66-6 C₁₁₄H₁₆₁N₁₅O₂₇S₂Si 
• 1240360-62-6 Z-Phe-Ala-Ser(tBu)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(TBS)-Asp(OtBu)-Ser(Bzl)-Asp-Glu(OcHx)-OBzl 

Relevant articles and documents

Total Synthesis and Structural Establishment/Revision of Antibiotics A54145

A54145 is a family of antibacterial cyclic lipodepsipeptides structurally resembling daptomycin. Since its discovery in 1990, only the ambiguous structures of the methoxy-aspartic acid (MeO-Asp) and the hydroxy-asparagine (HO-Asn) have been reported. We have developed efficient routes to obtain the fully protected l-MeO-Asp and l-HO-Asn building blocks compatible with Fmoc-SPPS, and a total synthesis of A54145 that enabled us to establish its structure, consisting of l-3S-HO-Asn and l-3R-MeO-Asp, revising the wrongly proposed structure of l-3S-MeO-Asp.

The role of phosphopeptides in the mineralisation of silica

We investigated the silicification activity of hyperphosphorylated peptides in combination with long-chain polyamines (LCPA). The bioinspired in vitro silicification experiments with peptides containing different amounts of phosphorylated serines showed structure-activity dependence by altering the amount and morphology of the silica precipitate. Our study provides an explanation for the considerable metabolic role of diatoms in the synthesis of hyperphosphorylated poly-cationic peptides such as natSil-1A1. The efficient late-stage phosphorylation of peptides yielded a synthetic heptaphosphopeptide whose silicification properties resemble those of natSil-1A1. As opposed to this, unphosphorylated poly-cationic peptides or LCPA require concentrations above 1 mM for silicification. Hyperphosphorylated peptides showed a linear dependence between the amount of dissolved peptides and the amount of precipitated silica in the concentration range below 1 mM. Under mildly acidic conditions and short precipitation times, the concentration of the added LCPA determined the size of the silica spheres.

Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles

(Chemical Equation Presented) Homochiral α-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde. The key feature of the sequence is a highly selective tandem Mitsunobu/3,3-sigmatropic rearrangement of hydrazoic acid that procures enantiomerically enriched allylic azides. The sequence is either terminated by oxidative cleavage to provide amino acids or by ring-closing metathesis to provide heterocycles or carbocycles bearing nitrogen.