N-α-Acetyl-L-argininamide acetate
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N-α-Acetyl-L-argininamide acetate

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Category
L-Amino Acids
Catalog number
BAT-002124
CAS number
1245401-04-0
Molecular Formula
C10H21N5O4
Molecular Weight
275.31
IUPAC Name
(2S)-2-acetamido-5-(diaminomethylideneamino)pentanamide;acetic acid
Synonyms
Ac-Arg-NH2 AcOH
InChI
InChI=1S/C8H17N5O2.C2H4O2/c1-5(14)13-6(7(9)15)3-2-4-12-8(10)11;1-2(3)4/h6H,2-4H2,1H3,(H2,9,15)(H,13,14)(H4,10,11,12);1H3,(H,3,4)/t6-;/m0./s1
InChI Key
KDWPITFWGMXUHM-RGMNGODLSA-N
Canonical SMILES
CC(=O)NC(CCCN=C(N)N)C(=O)N.CC(=O)O
1. Acetal-Based Functional Epoxide Monomers: Polymerizations and Applications
Jinsu Baek, Minseong Kim, Youngsin Park, Byeong-Su Kim Macromol Biosci. 2021 Nov;21(11):e2100251. doi: 10.1002/mabi.202100251. Epub 2021 Aug 8.
Protecting group chemistry is essential for various organic transformation and polymerization processes. In particular, conventional anionic ring-opening polymerization (AROP) often requires proper protecting group chemistry because it is typically incompatible with most functional groups due to the highly basic and nucleophilic conditions. In this context, many functional epoxide monomers with proper protecting groups are developed, including the acetal group as a representative example. Since the early introduction of ethoxyethyl glycidyl ether, there is significant development of acetal-based monomers in the polyethers. These monomers are now utilized not only as protecting groups for hydroxyl groups under AROP conditions but also as pH-responsive moieties for biomedical applications, further expanding their utility in the use of functionalized polyethers. Recent progress in this field is outlined from their synthesis, polymerization, and biomedical applications.
2. Photoacid-catalyzed acetalization of carbonyls with alcohols
Jason Saway, Abigail F Pierre, Joseph J Badillo Org Biomol Chem. 2022 Aug 10;20(31):6188-6192. doi: 10.1039/d2ob00435f.
In this report, we demonstrate that visible light photoactivation of 6-bromo-2-naphthol facilitates the photoacid-catalyzed acetalization of carbonyls with alcohols. We also demonstrate that 2-naphthol when coupled to a photosensitizer provides acetals from electron-deficient aldehydes. In addition, the S1 excited state pKa for 6-bromo-2-naphthol in water was determined and shown to have increased excited-state acidity relative to 2-naphthol.
3. Chemistry and biology of spiroacetals from myxobacteria
Michael Ricca, Mark A Rizzacasa Org Biomol Chem. 2021 Apr 7;19(13):2871-2890. doi: 10.1039/d1ob00026h. Epub 2021 Mar 8.
This review details the isolation, biosynthesis, biological activity and synthesis of spiroacetals from the myxobacterium Sorangium cellulosum. The strategies utilised to access the challenging structures and stereochemistry of these natural products are highlighted.
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