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47695

Sigma-Aldrich

Fmoc-Cys(Trt)-OH

≥95.0% (sum of enantiomers, HPLC)

Synonym(s):

N-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine, Nα-Fmoc-S-trityl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C37H31NO4S
CAS Number:
103213-32-7
Molecular Weight:
585.71
Beilstein/REAXYS Number:
4221286
MDL number:
MFCD00038538
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57651084
NACRES:
NA.26

Quality Level

100

assay

≥95.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D +16.0±2°, c = 1% in THF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

mp

170-173 °C (lit.)

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

OC(=O)[C@H](CSC(c1ccccc1)(c2ccccc2)c3ccccc3)NC(=O)OCC4c5ccccc5-c6ccccc46

InChI

1S/C37H31NO4S/c39-35(40)34(38-36(41)42-24-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)25-43-37(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34H,24-25H2,(H,38,41)(H,39,40)/t34-/m0/s1

InChI key

KLBPUVPNPAJWHZ-UMSFTDKQSA-N

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General description

Fmoc-Cys(Trt)-OH is an amino acid commonly used in the Fmoc solid-phase peptide synthesis.

Application

Fmoc-Cys(Trt)-OH is an N-terminal protected cysteine derivative used in peptide synthesis. Some of the examples are:
  • Synthesis of mono- and bi-functionalized platinum(IV) complexes to target angiogenic tumor vasculature.
  • Synthesis of proteins through native chemical ligation of peptide hydrazides as thioester surrogates via solid-phase synthesis.
  • Synthesis of glycoconjugates by conjugating reducing sugars to cysteine residues of peptides.

Storage Class

11 - Combustible Solids

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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Conjugated platinum (IV)? peptide complexes for targeting angiogenic tumor vasculature.
Mukhopadhyay S, et al.
Bioconjugate Chemistry, 19(1), 39-49 (2007)
A double-click approach to the protecting group free synthesis of glycoconjugates.
Alexander S R, et al.
Organic & Biomolecular Chemistry, 16(8), 1258-1262 (2018)
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Zheng J S, et al.
Nature Protocols, 8(12), 2483-2483 (2013)
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Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 18(1), 198-207 (2018-11-14)
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