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15500

Sigma-Aldrich

Boc-Ser-OH

≥99.0% (T), for peptide synthesis

Synonym(s):

N-(tert-Butoxycarbonyl)-L-serine, Boc-L-serine

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About This Item

Linear Formula:
HOCH2CH(COOH)NHCOOC(CH3)3
CAS Number:
3262-72-4
Molecular Weight:
205.21
Beilstein/REAXYS Number:
2212252
EC Number:
221-867-3
MDL number:
MFCD00037243
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57647375
NACRES:
NA.22

product name

Boc-Ser-OH, ≥99.0% (T)

Quality Level

100

assay

≥99.0% (T)

optical activity

[α]20/D −3.5±0.5°, c = 2% in acetic acid

reaction suitability

reaction type: Boc solid-phase peptide synthesis

mp

91 °C (dec.) (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)N[C@@H](CO)C(O)=O

InChI

1S/C8H15NO5/c1-8(2,3)14-7(13)9-5(4-10)6(11)12/h5,10H,4H2,1-3H3,(H,9,13)(H,11,12)/t5-/m0/s1

InChI key

FHOAKXBXYSJBGX-YFKPBYRVSA-N

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General description

Boc-Ser-OH is an amino acid derivative.

Application

Boc-Ser-OH may be used in the synthesis of the following:
  • 2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl; Boc: t-butyloxycarbonyl)
  • Boc-Ser-Leu-OMe
  • cyclic peptide synthesis
  • benzylsulfonyl-D-Ser-Ser-4-amidinobenzylamide
Building block in peptide synthesis. Starting material for the synthesis of various α-amino acids via the β-lactone.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Fmoc-Ser(tBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47619

Fmoc-Ser(tBu)-OH

Synthesis of cyclic peptides via O-N-acyl migration.
Lecaillon J, et al.
Tetrahedron Letters, 49(31), 4674-4676 (2008)
The relationship between taste and primary structure of ?delicious peptide?(Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from beef soup.
Tamura M, et al.
Agricultural and Biological Chemistry, 53(2), 319-325 (1989)
Michael R Carrasco et al.
Biopolymers, 84(4), 414-420 (2006-03-02)
Amino acids with N-alkylaminooxy side chains have proven effective for the rapid synthesis of neoglycopeptides. Chemoselective reaction of reducing sugars with peptides containing these amino acids provides glycoconjugates that are structurally similar to their natural counterparts. 2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl;
O García-Suárez et al.
Immunology, 94(2), 235-241 (1998-09-19)
Increasing evidence suggests that some members of the neurotrophic factor family of neurotrophins could be implicated in the regulation of immune responses. Neurotrophins, as well as their tyrosine kinase signal-transducing receptors (the so-called Trk neurotrophin receptors), have been detected in
Gema Villa-Fombuena et al.
Development (Cambridge, England), 148(18) (2021-08-10)
Drosophila female germline stem cells (GSCs) are found inside the cellular niche at the tip of the ovary. They undergo asymmetric divisions to renew the stem cell lineage and to produce sibling cystoblasts that will in turn enter differentiation. GSCs
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