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Current Project
Chemical
Nomenclature and Structure Representation Division (VIII)
Number: 2004-024-1-800
Title: Nomenclature of cyclic peptides
Task Group
Chairman: Gerard P.
Moss
Members: IUBMB-IUPAC
Joint Commission on Biochemical Nomenclature (JCBN)
Objective:
To extend rule 3AA-19.5 of the Nomenclature
and Symbolism for Amino Acids and Peptides (Recommendations 1983)
to cover all classes of cyclic peptides.
Description:
Cyclic peptides are briefly considered in the Nomenclature and Symbolism
for Amino Acids and Peptides (recommendations 1983) [1] in part 2 under
symbolism (see 3AA-19.5). There are no recommendations on naming these
peptides. This deficiency will be rectified by the proposed recommendations
which will be based on the established procedures for naming peptides
[1] and recommendation RF-4.3 in Revised Section F: Natural Products
and Related Compounds (IUPAC Recommendations 1999) [3], rule C-44.1
and C-212.2 of the IUPAC Nomenclature of Organic Chemistry (1979) [4],
R-1.2.6.1 and R-5.5.4.4 of A Guide to IUPAC Nomenclature of Organic
Chemistry (1993) [5] and rule 2-Carb-26 of the Nomenclature of Carbohydrate
[6].
The recommendations will include rings generated from an acyclic peptide
by formation of a peptide or ester bond; by a disulfide link; or by
a new carbon-carbon, carbon-nitrogen, nitrogen-oxygen or carbon-sulfur
bond (not esters or amides). These new bonds are indicated by the prefix
anhydro, cyclo or epoxy, or combinations of them. The inclusion of modified
standard amino acids or amino acids not related to standard amino acids
will be considered. Any stereochemistry generated by ring formation
will be indicated using standard organic conventions.
References
- JCBN, Nomenclature and Symbolism for Amino Acids
and Peptides, Recommendations 1983, Biochem. J. 219,
345-373 (1984); Eur. J. Biochem. 138, 9-37 (1984) and
152, 1 (1985); Int. J. Pept. Prot. Res. 24, following
p. 84 (1984); J. Biol. Chem. 260, 14-42 (1985); Pure
Appl. Chem. 56, 595-624 (1984); 'Amino Acids and Peptides'
(Jones, J.H., ed.) Specialist Periodical Report, The Royal Society
of Chemistry, 16, 387-410 (1985), and also on pp. 39-67 in [2].
- IUBMB (1992) Biochemical Nomenclature and Related
Documents, 2nd edition, Portland Press, London.
- IUPAC Commission on the Nomenclature of Organic
Chemistry (CNOC), Nomenclature of Organic Chemistry, Revised Section
F: Natural Products and Related Compounds, (IUPAC Recommendations
1999), Pure Appl. Chem. 71, 587-643 (1999).
- IUPAC (1979) Nomenclature of Organic Chemistry,
Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford.
- IUPAC (1993) A Guide to IUPAC Nomenclature of
Organic Chemistry, Recommendations 1993, Blackwell Scientific
Publications, Oxford.
- JCBN, Nomenclature of Carbohydrate, Recommendations
1996, Adv. Carbohydr. Chem. Biochem. 52, 43-177 (1997),
Carbohydr. Res. 297, 1-90 (1997), J. Carbohydr. Chem.
16, 1191-1280 (1997), Pure Appl. Chem. 68, 1919-2008
(1996).
Progress:
In June 2004, a draft arising from the work carried out under the
auspices of the IUPAC-IUBMB Joint Commission on Biochemical Nomenclature
has been made available to Division VIII for comments. After that initial
review period a revised version will be prepared for public review.
A draft document is submitted to public review comments until 31 March
2005> see provisional
recommendations
Last update: 26 October 2004
<project announcement to be published
in Chem. Int. >
Page last modified 15 March 2005
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