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47695

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:
Molecular Weight:
585.71
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
MDL number:
Beilstein/REAXYS Number:
4221286

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Product Name

Fmoc-Cys(Trt)-OH, ≥95.0% (sum of enantiomers, HPLC)

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

SMILES string

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

InChI key

KLBPUVPNPAJWHZ-UMSFTDKQSA-N

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

Quality Level

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1 of 4

This Item
476314751647639
assay

≥95.0% (sum of enantiomers, HPLC)

assay

≥95.0% (HPLC)

assay

≥98.0% (HPLC)

assay

≥98.0% (sum of enantiomers, HPLC)

functional group

Fmoc

functional group

Fmoc

functional group

Fmoc

functional group

Fmoc

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

optical activity

[α]20/D +16.0±2°, c = 1% in THF

optical activity

[α]20/D −83±2°, c = 1% in ethyl acetate

optical activity

-

optical activity

[α]/D 87±5°, c = 1 in chloroform

mp

170-173 °C (lit.)

mp

73-77 °C

mp

-

mp

-

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.[1]
  • Synthesis of proteins through native chemical ligation of peptide hydrazides as thioester surrogates via solid-phase synthesis.[2]
  • Synthesis of glycoconjugates by conjugating reducing sugars to cysteine residues of peptides.[3]

General description

Fmoc-Cys(Trt)-OH is an amino acid commonly used in the Fmoc solid-phase peptide synthesis. [4]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Parallel synthesis of structurally diverse aminobenzimidazole tethered sultams and benzothiazepinones
Sureshbabu D et al.
Tetrahedron Letters, 53, 6897-6900 (2012)
Chemical synthesis of proteins using peptide hydrazides as thioester surrogates.
Zheng J S, et al.
Nature Protocols, 8(12), 2483-2483 (2013)
Panchada Ch V Govindu et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 18(1), 198-207 (2018-11-14)
Avobenzone is the most widely used UVA filter in sunscreen lotion and it is prone to degradation in the presence of sunlight/UV radiation. To overcome the photo-instability of avobenzone, various photostabilizers have been used as additives, including antioxidants such as
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)

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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