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47619

Sigma-Aldrich

Fmoc-Ser(tBu)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Fmoc-O-tert-butyl-L-serine

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About This Item

Empirical Formula (Hill Notation):
C22H25NO5
CAS Number:
71989-33-8
Molecular Weight:
383.44
Beilstein:
3632013
EC Number:
276-260-6
MDL number:
MFCD00037127
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57651041
NACRES:
NA.26

product name

Fmoc-Ser(tBu)-OH, ≥98.0% (HPLC)

Assay

≥98.0% (HPLC)

form

powder

optical activity

[α]20/D +25.5±1°, c = 1% in ethyl acetate

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C22H25NO5/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)/t19-/m0/s1

InChI key

REITVGIIZHFVGU-IBGZPJMESA-N

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Application

Fmoc-Ser(tBu)-OH is an N-terminal protected reagent used in the peptide synthesis. Some of the reported examples are:
  • Total synthesis of an antibiotic, daptomycin, by cyclization via a chemoselective serine ligation.
  • Preparation of MUC1, a T-cell helper peptide, using iterative pentafluorophenyl ester-mediated fragment condensations.
  • Linear solid-phase peptide synthesis of ubiquitin and diubiquitin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Total synthesis of daptomycin by cyclization via a chemoselective serine ligation.
Lam H Y, et al.
Journal of the American Chemical Society, 135(16), 6272-6279 (2013)
Self?Adjuvanting Multicomponent Cancer Vaccine Candidates Combining Per?Glycosylated MUC1 Glycopeptides and the Toll?like Receptor 2 Agonist Pam3CysSer.
Wilkinson B L, et al.
Angewandte Chemie (International Edition in English), 50(7), 1635-1639 (2011)
Advances in proline ligation.
Townsend S D, et al.
Journal of the American Chemical Society, 134(8), 3912-3916 (2012)
Chemical synthesis of ubiquitin, ubiquitin?based probes, and diubiquitin.
El Oualid F, et al.
Angewandte Chemie (International Edition in English), 49(52), 10149-10153 (2010)
R Ashton Lavoie et al.
Biotechnology and bioengineering, 117(2), 438-452 (2019-10-28)
The clearance of host cell proteins (HCPs) is of crucial importance in biomanufacturing, given their diversity in composition, structure, abundance, and occasional structural homology with the product. The current approach to HCP clearance in the manufacturing of monoclonal antibodies (mAbs)
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