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H54409

Sigma-Aldrich

trans-4-Hydroxy-L-proline

≥99%, for peptide synthesis

Synonym(s):

(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp

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About This Item

Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein:
81441
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22
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Product Name

trans-4-Hydroxy-L-proline, ≥99%

Quality Level

Assay

≥99%

form

crystalline powder

optical activity

[α]25/D −75.6°, c = 1 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

color

white to off-white

mp

273 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

O[C@H]1CN[C@@H](C1)C(O)=O

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

InChI key

PMMYEEVYMWASQN-DMTCNVIQSA-N

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General description

Trans-4-hydroxy-L-proline is an isomer of hydroxyproline used as a chiral building block in the production of many pharmaceuticals like neuroexcitatory kainoids.[1]

Application

Versatile reagent for the synthesis of neuroexcitatory kainoids[2] and antifungal echinocandins.[3] Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.[4]

Other Notes

Natural constituent of animal structural proteins such as collagen and elastin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthetic Communications, 23, 2691-2691 (1993)
Biosynthesis of trans-4-hydroxyproline by recombinant strains of Corynebacterium glutamicum and Escherichia coli
Yi Y, et al.
BMC biotechnology, 14, 1-8 (2014)
Tetrahedron Letters, 35, 6163-6163 (1994)
Tetrahedron, 49, 6195-6195 (1993)
Jacob Kofoed et al.
Chemical communications (Cambridge, England), (14)(14), 1482-1484 (2006-04-01)
The aldol reaction of acetone with aldehydes in aqueous medium under catalysis by zinc-proline (Zn(L-Pro)2) and secondary amines such as proline, (2S,4R)-4-hydroxyproline (Hyp) and (S)-(+)-1-(2-pyrrolidinomethyl)pyrrolidine (PMP) is shown to proceed by an enamine mechanism, as evidenced by reductive trapping of

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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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  3. Guten Tag, ist der Stoff zur äußerlichen und innerlichen Anwendung geeignet?

    1 answer
    1. Unless otherwise stated this product is intended for research use only and is not to be used for any other purpose, which includes but is not limited to, unauthorized commercial uses, in vitro diagnostic uses, ex vivo or in vivo therapeutic uses, or any type of consumption or application to humans or animals.

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