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Sigma-Aldrich

Fmoc-Lys(Boc)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Nα-Fmoc-Nε-Boc-L-lysine

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About This Item

Empirical Formula (Hill Notation):
C26H32N2O6
CAS Number:
71989-26-9
Molecular Weight:
468.54
Beilstein:
4217767
EC Number:
276-256-4
MDL number:
MFCD00037138
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57651044
NACRES:
NA.26
Pricing and availability is not currently available.

Product Name

Fmoc-Lys(Boc)-OH, ≥98.0% (HPLC)

Assay

≥98.0% (HPLC)

form

solid

optical activity

[α]20/D −12±1°, c = 1% in DMF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Boc
Fmoc

storage temp.

2-8°C

SMILES string

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

InChI

1S/C26H32N2O6/c1-26(2,3)34-24(31)27-15-9-8-14-22(23(29)30)28-25(32)33-16-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h4-7,10-13,21-22H,8-9,14-16H2,1-3H3,(H,27,31)(H,28,32)(H,29,30)/t22-/m0/s1

InChI key

UMRUUWFGLGNQLI-QFIPXVFZSA-N

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General description

Fmoc-Lys(Boc)-OH is an amino acid derivative used as a reagent in Fmoc solid-phase peptide synthesis.[1][2]

Application

Fmoc-Lys(Boc)-OH can be used for:
  • The solid-phase synthesis of pentasubstituted dihydroimidazolylbutyl dihydroimidazol-3-ium salts by coupling with p-methylbenzhydrylamine (MBHA) resin.[3]
  • Fmoc-based peptide synthesis of bis-naphthalene diimide, a threading intercalator.[4]
  • Synthesis of ε-Boc-ε-(3,5-bis-trifluoromethyl-benzyl)-α-Fmoc-L-Lysine to be used as 19F NMR based screening tool.[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8473
BCCK5911
BCCJ1479
BCCH5087
BCCG3746

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Solid-phase parallel synthesis of substituted dihydroimidazolylbutyl dihydroimidazol-3-ium salts.
Acharya AN, et al.
Tetrahedron Letters, 43(7), 1157-1160 (2002)
Improved synthesis of polyfluorinated l-lysine for 19F NMR-based screening.
Malgesini B, et al.
Molecular Diversity, 13(1), 53-56 (2009)
Marta Kulik et al.
Biochimie, 138, 32-42 (2017-04-12)
A fragment of 23S ribosomal RNA (nucleotides 1906-1924 in E. coli), termed Helix 69, forms a hairpin that is essential for ribosome function. Helix 69 forms a conformationally flexible inter-subunit connection with helix 44 of 16S ribosomal RNA, and the nucleotide
Marine Bacchi et al.
Protein science : a publication of the Protein Society, 25(12), 2225-2242 (2016-09-28)
Synthetic biology (or chemical biology) is a growing field to which the chemical synthesis of proteins, particularly enzymes, makes a fundamental contribution. However, the chemical synthesis of catalytically active proteins (enzymes) remains poorly documented because it is difficult to obtain
Bis-naphthalene diimide exhibiting an effective bis-threading intercalating ability.
Nojima T, et al.
Nucleic Acids Symposium Series, 3(1), 123-124 (2003)
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Questions

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  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/449/386/product-dating-information-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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